Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
1.2.1.1.6 Carbohydrate-Based and Related Ketones

DOI: 10.1055/sos-SD-204-00417

Wong, O. A.; Ramirez, T. A.; Shi, Y.Science of Synthesis: Asymmetric Organocatalysis, (20121789.

Fructose-derived ketone 39 epoxidizes E-disubstituted and trisubstituted alkenes 62 to give products 63 with high enantioselectivities (Scheme 7).[‌59‌,‌60‌] Structural studies have revealed that the presence of methyl groups on the spiroketal group is an important feature. Variations such as those in ketones 40, 41, and 43 decrease the enantioselectivities for E-disubstituted and trisubstituted alkenes.[‌61‌,‌62‌] The 1,4-dioxan-2-yl group in 45 is inferior to the five-membered ketal group in 39.[‌61‌] The pyranose oxygen in ketone 39 is also important for the enantioselectivity, as determined by comparison to ketone 46.[‌34‌] Structural variations of the fused ketal group of ketone 39 have also been studied (47 and 48).[‌63‌‌65‌] The oxazolidinone and ester groups were installed with the hope that the replacement of the fused ketal in 39 by more electron-withdrawing groups would reduce the decomposition of the catalyst via BaeyerVilliger oxidation under the reaction conditions. As a result, only 15mol% catalyst is required for ketone 47 to obtain results comparable to those of ketone 39. Glucose-derived ketone 49 is an effective catalyst for cis-alkenes and styrenes.[‌66‌‌68‌] Variants of ketone 49 such as N-aryl-substituted ketones 5052 are all effective catalysts for cis-alkenes and styrenes.[‌69‌,‌70‌] Morpholinone-containing ketones 54 and 55 have also been investigated.[‌71‌,‌72‌] Several examples of other carbohydrate-derived ketones are also listed in Scheme 7. Good to high enantioselectivities for the epoxidation of selected alkenes are obtained using these ketones.

Meeeee 8 Meeeeeeeee Meeeeeeeeee eeee Meeeee Meeeeeeeeeee-Meeee Meeeeee[‌88‌,‌88‌‌88‌]

Meeeeeeeeee 8

M8 M8 M8 Meeeee Meeeee ee (%) Mee
Me M Me 88 88 [‌88‌,‌88‌]
Me M Me 88 88 [‌88‌,‌88‌]
Me Me Me 88 88 [‌88‌,‌88‌]
Me (MM8)8 88 88 [‌88‌,‌88‌]
Me M M 88 88 [‌88‌,‌88‌]
Me M Me 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M M 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M M 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M M 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M M 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M M 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M M 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M M 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M Me 88 88 [‌88‌,‌88‌]
Me M Me 88 88 [‌88‌,‌88‌]
Me (MM8)8 88 88 [‌88‌,‌88‌]
Me M M 88 88 [‌88‌,‌88‌]
Me M Me 88 88 [‌88‌‌88‌]
Me M Me 88 88 [‌88‌‌88‌]
Me (MM8)8 88 88 [‌88‌‌88‌]
Me M M 88 88 [‌88‌‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M M 88 88 [‌88‌]
Me M M 88 88 [‌88‌,‌88‌]
Me M M 88 88 [‌88‌]
Me M Me 88 88 [‌88‌,‌88‌]
Me M Me 88 88 [‌88‌,‌88‌]
Me (MM8)8 88 88 [‌88‌,‌88‌]
Me M Me 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me Me Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me Me Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me Me Me 88 88 [‌88‌]
Me (MM8)8 88 88 [‌88‌]
Me M Me 88 88 [‌88‌]
Me M M 88 88 [‌88‌]

Meee eee eeee eeeeeeeee ee Meeeeee 88, M-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeee eeeeeeee eeeeee eeeeeeeee eeeeee ee ee eee eeee eeeeeeeee eeee ee eeeeeeeee. Mee ee eeeee eeee, eeeeeeee eeeeeeeeeeee eee eeee ee eeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeeeeeeee, eeee eeeeeeeee eeeeee eeeeeeeeeeeeeeeeeeee. Me eee eeeee eeee, M-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeeeeee eeeeeeee eeeeeeeeeeee eee eeee eeeeeeeeeee eeeeeeeeee. Meeeeee, eeeeeeee-eeeeeee eeeeee 88 eee eeee eeeee ee eeeeeeeeeeee eeeeeee eeee eeeeeeeeeeeeeeeeeeee eee M-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeee ee eeeeeee eeeeeeee eeeeeeeeeeee.[‌88‌,‌88‌] Meeeee 88 eeee eeeeeeee eeee eeeeeeeeeeeeeeeeeeee eee eee eeeeeeeeeeee ee eeeeeeeeeeee,[‌88‌] eeeeeeeeeeeeee,[‌88‌] eeee eeeeee, eeee eeeeee,[‌88‌‌88‌] eeeeeeeeee eeeeee,[‌88‌] eee eeeeee[‌88‌,‌88‌] (Meeee 8). Mee eeeeeeeeee ee eeeeee 88 (eee-88) ee eeee eeeeeee eeeeeeeee eeee e-eeeeeee.[‌88‌,‌88‌] M eeeeeeeeeee ee eeeeeeee eeeeeeee eee e eeeeeee (eeee ee eeeeeeeeeeee) eee eeee ee eeee ee eee eeeeeee. Meee eeee eeeeee eeeeeeee eeeeeee eeeeeee eeeeeeee ee eee eeeeeeeeeeeeee eeee Meeee eeeeeeeeee.[‌88‌‌88‌] Me eeeeeee, eee eeeeeeeee ee (M)-eeeeeeee (88) ee eeeee-8,8-eeeeeeeeeeeeeee (88), ee eeeee ee Meeeee 8.[‌88‌]

Meeee 8 Meeeeeee Meeeeeeeee Meeeeeeeeee Meeeeee Meeee e Meeeeeee Meeeeeee Meeeeee Meeeee[‌88‌,‌88‌‌88‌,‌88‌‌88‌]

Meeeeeee Meeeeeee eee% ee 88 Meeeeeeeee Meeeeee Meeee (%) ee (%) Mee
88 MeMM/MM8(MMe)8/ee eeeeee (8:8:8), 88°M, 8e 88 88 [‌88‌]
88 MeMM/MM8(MMe)8/ee eeeeee (8:8:8), 88°M, 8e 88 88 [‌88‌]
88 MeMM/MM8(MMe)8/ee eeeeee (8:8:8), 8°M, 8e 88 88 [‌88‌]
88 MeMM/MM8(MMe)8/ee eeeeee (8:8:8), 8°M, 8e 88 88 [‌88‌]
88 MeMM/MM8(MMe)8/ee eeeeee (eM8.8) (8:8:8), 88°M, 8e 88 88 [‌88‌]
88 MeMM/MM8(MMe)8/ee eeeeee (eM8.8) (8:8:8), 88°M, 8e 88 88 [‌88‌]
88 MeMM/MM8(MMe)8/ee eeeeee (8:8:8), 8°M, 8.8e 88 88 [‌88‌]
88 MeMM/MM8(MMe)8/ee eeeeee (eM8.8) (8:8:8), 8°M, 8e 88 88 [‌88‌,‌88‌]
88 MeMM, ee eeeeee, 8°M, 8e 88 88 [‌88‌,‌88‌]
88 MeMM, ee eeeeee, 8°M, 8.8e 88 88 [‌88‌,‌88‌,‌88‌]

Meeeee 8 Meeeeeeeeee Meeee e Meeeeeee Meeeeeee Meeeeee Meeeee eee Meeeeeee Meeeeeee/Meeeeeeeeeee ee Meeeeee[‌88‌]

M eeeeeeeeee eeeee eeeee eee eee eeeeeeeeeee ee M-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeeee eeeeee 88 eee eeee eeeeeeeeeee (Meeeee 8).[‌88‌,‌88‌] Meee eeeeeeeeee eeeee eeeee eee eeee eeee ee eeeeeeeeee eeeeeee eee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeee eeeeeeee. Mee eeeeeeeeeee eeee eeeeee 88 eeeeeeee eeeeee eeeeeee eeeee eeeeeeeeee eeeee 88 eeee eeeeee eeeeeeeeee eeeee 88 eeeee eee eeeee eeeeeeeee eeeeeeeeee eeeee. Meee ee eeeee eeeeeeeeee eeeeee eee eeeeeeeeee eeeeeeee; eeeeeee, eeeee 88 ee eeeeeeeee eeeeeee eeee eeeeee 88 ee e eeeeee ee e eeeeeeeeee eeeeeeeeeee eeeeeee eeeeeeeeeee eeeeeee eee eeee eeee ee eee eeeeeeeee eeeeee eee eee π* eeeeeee ee eee eeeeeeee eeeeee.[‌88‌,‌88‌] Me eeeeeeee, eeeee 88 eee ee eeeeeee eeeeeee eeee eeeeee 88 ee eeeeeeeeee eee eeee ee M8 eee/ee eeeeeeeeee eee eeee ee M8.

Meeeee 8 Meeee eee Meeeee Meeeeeeeee Meeeee eee eee Meeeeeeeeee eeee e Meeeeeee-Meeeeee Meeeee[‌88‌,‌88‌]

Meeeeee eeeeeeeeee eeeeeeeeee ee eeeeee 88 eeee eeee eeee eeeeeee. Meeee eeeee, eeeeee 88 eeeee e eeeeeeeeeee eeeeeeeeeee ee eeeeeeee eeeeeeeeee (Meeee 8).[‌88‌,‌88‌] M eeeeeee ee eeee eeeeeeee eeeeeee eeee ee α,β-eeeeeeeeeee eeeeee eee eeeee-eeeeeeee eee eeeeeeeeee ee eeee eeeeeeeeeeeeeeeeeeee eee eeee eeeeee. M eeeeee ee eee-eeeeeee eee eeee ee eeeeeeeeee eeee eeee eeeeeeeeeeeeeeeeeeee eeeee eeeeee 88. Mee eeeeeee eeeeeee eeee eee eeee eeeee eee eeeeee eeeeeeeeeee ee eee eee-eeeeeeeeeeee, eee eeeeee eee eeeeeeeeeeeeeeeeee eee eee eeeeeeeee eeeeeee. Meeeee 88 eee eeeeee eeee eee eeeeeee eeee eeeee eee eeeeee 88 eee eee eeeeeee (88M8M) eeee eeeeeee eeeeeee eee eee eeeeeeeeeee.

Meeee 8 Meeeeeee Meeeeeeeee Meeeeeeeeee Meeeeee Meeee ee Meeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeee[‌88‌,‌88‌]

Meeeeeee Meeeeeee eee% ee 88 Meeeeeeeee Meeeeee Meeee (%) ee (%) Mee
88 MeMMM8, MeMM/M8M (8.8:8), 8°M, 88e 88 88 [‌88‌]
88 MeMMM8, MeMM/M8M (8.8:8), 8°M, 88e 88 88 [‌88‌]
88 MeMMM8, MeMM/M8M (8.8:8), 8°M, 88e 88 88 [‌88‌]
88 MeMMM8, MeMM/M8M (8.8:8), 8°M, 88e 88 88 [‌88‌]
88 MeMMM8, MeMM/M8M (8.8:8), 8°M, 88e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]
88e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 88e 88 88 [‌88‌]
88 MeMMM8, MeMM/M8M (8.8:8), 8°M, 88e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]
8.8e M8MM8, MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8), 8°M, 8e 88 88 [‌88‌]

e Mee eeeeeeee eee eeee ee eee eeeeeee (88M8M).

Meeeeeee eee eee-eeeeeee eeee eeeeee ee ee eeeeeeeeeee eeeeeeeeee eee eeeeeeeeee eeeeeeeeeee. Meeeeeeeeeeee-eeeeeeeeee eeeeee 88 ee e eeee eeeeeeeee eeeeee eee eee eeeeeeeeeee ee eee-eeeeeee (e.e., 88) eee eeeeeeee ee eeee eee eee-eeeeeeee (e.e., 88) (Meeee 8).[‌88‌‌88‌,‌88‌] Meeeeeeeeeeee ee eee eeeeeeee ee eee eeeeeeeeeee ee eeeeeee eeeeeee. Me eeeee eeeee, eeee eee-eeeeeeee eee eeeeeeee eeee eee-eeeeeee. M eeee eeeeee eeeeeeeeee eeeeee ee eeeeeee 8888, 88, eee 88 (Meeeee 8) eeee eee eeeeeeeeeeee eeeeeee ee eeeeee 88 eeee eeee eeee eeeeeeeee. Meeeeee 88 eee 88, ee eeeeeeeeee, eee ee eeeeeeee ee e eeeee eeeee.[‌88‌] Meeeeee 8888, 88, eee 88 eeeeeee eeee eeeeeeeeeeeeeeeeeeee eee eee eeeeeeeeeee ee (M)-8-eeeeeeeeee-8-eeee,[‌88‌] eeeeeeeeeee (e.e., eeeeeeeeeee ee 88 ee eeee 88),[‌88‌] eeeeeeee,[‌88‌] eee-eeeeee,[‌88‌] eee-eeeeee,[‌88‌] eeeeeeeeeeeeeeeeeeeeeee,[‌88‌,‌88‌] eeeeeeeeeeeeeeeeeeeeeeee,[‌888‌] eee eeeeeeeeeeee eee-eeeeeee[‌888‌] (Meeee 8). Meeeeeee eeeeeeee/eeeeeeeeeeee eee eeee eeee eeeeeeee ee eee eeeeeee eee eee eeeeeeeeeee eeeee eeeeee 88, eee eeeeeee ee eee eeeeeeeee ee 8-eeeeee-8-eeeeeeeeee-8-eee (88) ee 8,8-eeeeeeee-8-eeeeeeeeeeeee (88) (Meeeee 88).[‌888‌]

Meeee 8 Meeeeeee Meeeeeeeee Meeeeeeeeee Meeeeee Meeee ee Meeeeeeeeeeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeee[‌88‌‌88‌]

Meeeeeee Meeeeeee eee% ee 88 Meee (°M) Meeeeee Meeee (%) ee (%) Mee
88 88 88 88 [‌88‌,‌88‌]
88 88 88 88 [‌88‌]
88 88 88 88 [‌88‌,‌88‌]
88 88 88 88 [‌88‌,‌88‌]
88 8 88 88 [‌88‌,‌88‌]
88 88 88 88 [‌88‌,‌88‌]
88 88 88 88 [‌88‌,‌88‌]
88 88 88 88 [‌88‌]
88 88 88 88 [‌88‌,‌88‌]
88 88 88 88 [‌88‌,‌88‌]

Meeee 8 Meeeeeee Meeeeeeeee Meeeeeeeeee Meeeeee eee Meeeeee Meeeeeeeeeeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeeee[‌88‌‌88‌,‌88‌‌888‌]

Meeeeeee Meeeeeee Meeeee Meeeee (eee%) Meeeeeeeee Meeeeee ee (%) Mee
88 (88) MMM, ee eeeeee (eM8.8), 88°M, 8.8e 88 [‌88‌]
88 (88) MMM, ee eeeeee (eM8.8), 88°M, 8.8e 88 [‌88‌]
88 (88) MMM, ee eeeeee (eM8.8), 88 ee 88°M, 88e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8.8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8.8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 88e 88 [‌88‌,‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 [‌88‌]
88 (88) MMM/ee eeeeee (eM8.8) (8.8:8), 88°M, 8e 88 [‌88‌]
88 (88) MMM/ee eeeeee (eM8.8) (8.8:8), 8°M, 88e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88 ee 8°M, 888e 88e [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88 ee 8°M 88e [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e, eeee 8°M, 8e e [‌888‌]
88 (88) MMM, ee eeeeee (eM8.8), 8°M, 8e 88 [‌888‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 [‌888‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e e [‌888‌]

e Mee eeeeeee eee eeeeeeeeeeee eeeeeeeeeee eeee eeeeee eeeeeeeeee ee 8-eeeeeeeeeeeeeeeeeeee eeee 88% ee.

e Mee eeeeeee eee eeeeeeeeeeee eeeeeeeeeee eeee (M)-8-eeeeee-8-eeeeeeeeeeeeeeeeeeee eeee 88% ee.

e Meeeeeeeeeee eeeeee ee eeeeeee eee eeeeeeee; eeeeeee eee eeeeeeeeeeee eeeeeeeeeee eeee (M)-8-eeeeee-8-eeeeeeeeeeeeeeeeee-8(8M)-eee eeee 88% ee.

e Meeeeeeeeeee eeeeee ee eeeeeee eee eeeeeeee; eeeeeee eee eeeeeeeeeeee eeeeeeeeeee eeee (M)-8-[(M)-8-eeeeeeeeeeee]eeeeeeeeeeee-8(8M)-eee eeee 88% ee.

Meeeee 88 Meeeeeeeeee Meeee ee Meeeeeeeeeeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeee eee Meeeeeee Meeeeeee/Meeeeeeeeeee ee Meeeeee[‌888‌]

Meee eeeeeeee eee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeee eeeeeeee, ee eee eeeeeeee eeee ee eee eeeeeeeeee eeeee, eee eeeeeeee ee eeeeeeeeeee eeeeeeeeeee ee eee eee- ee eeeeeeee eeeeee eeeeeee ee ee eeee ee eee eeeeeeeeeeeeeeeeee ee eeeeeee 8888, 88, eee 88. Meeee eeeee ee ee ee eeeeeeeeee eeeeeeeeeee eeeeeee eee eeeeeeee/eeeeeeeeeee eeeeeeeeeeee ee eee eeeeee eee eee eeeeeeeeeeeee eeeeee ee eee eeeeeeee.[‌88‌‌88‌] Meee eeeeeeeeeee eeeeee eeeee eeeeeeeeee eeeee 88 ee ee eeeeeee eeee eeeee eeeeeeeeee eeeee 88 (Meeeee 88). Mee eee eeeeeeeeeee ee eeeeeee eeeeeeeeeeee eeeeeee, eee eeeeeeeeeeeeeeeeee eeeeee eeeeeee eeee e eeeeeeeeeee eeeeeeeeeee eeeeeee eee eeeeee eeeeeeeeeee ee eee eeeeeeeee eee eee M-eeeeeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee Meeee Meeeeeeeee Meeeee eee eee Meeeeeeeeee eeee Meeeeeeeeeeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeeee[‌88‌‌88‌]

Meeee eeee eee- eee eeeeeeee eeeeeee, 8,8-eeeeeeeeeeeee eeeeeee eeeeeeeee eeeeeee eeeee ee eeeeeeeeeee eeeeeeeeee. Meeeeeeeeeee-eeeeeeeeee eeeeee 88 ee e eeeeeeeee eeeeeeee eee eeee eeeee ee eeeeee (Meeee 8).[‌88‌] Me ee 88% ee eee ee eeeeeeee eee e eeeeee ee 8,8-eeeeeeeeeeeee eeeeeee. Meee eeeeeeeeeee eeeeee eeeeeeee eee e eeeeee-eeee eeeeeeeeee eeeee 88 (Meeeee 88). Me eeeeeee, e eeeee eeeeeeeeee eeeee ee eeeeeee eee ee eee eeeeeeeeeee eeeeeeeeeee eeeeeee eee π* eeeeeee ee eee eeeeeeee eeeeee eee eee eeee eeee ee eee eeeeeeeee eeeeee. Meeeeee, ee eeee eeee, eee eeeeeeeeee eeeeeeeeeee eeeeeee eee eeeeeeee eeeeeeeeeee ee eee eeeeee eee eee eeeeeeeeeeee eeeeee ee eee eeeeee eeeeeeeeee eeeeeeeee eee eeeeeeeeeee eeeeeee eeeeeeeeeee eee eeeeee eeeeee eeeeeeeeee eeeee 88 ee ee eeeeeee eeee eee eeeee eeeeeeeeee eeeeee 8888. Me eeeeeeee ee 8,8-eeeeeeeeeeeee eeeeeee, eeeeee 88 eeee eeeeeeee eeee eeeeeeeeeeeeeeeeeeee eee eeee eee- eee eeeeeeeeeeeeee eeeeeee (Meeee 8).

Meeee 8 Meeeeeee Meeeeeeeee Meeeeeeeeee Meeeeee Meeee e Meeeeeeeeeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeee[‌88‌]

Meeeeeee Meeeeeee Meeeeeeeee Meeeeee Meeee (%) ee (%) Mee
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
8,8-eeeeeee, ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]
MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 88 [‌88‌]

Meeeee 88 Meeee eee Meeeee Meeeeeeeee Meeeee eee eee Meeeeeeeeee eeee e Meeeeeeeeeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeee[‌88‌,‌88‌]

Meeeeeee-eeeeeee eeeeee 88 eee eeeeeee-eeeeeee eeeeeee 8888, 88, eee 88 eeee eeeeee eeeeeeee eee eeeeeeeee eeeeee. Meee eee eeeeeeeeeee eeeeee eeee eee eeeee ee eeeee eeeeeee, eeeeee 88 eee eeeeeeee ee eeeeeee eee eeeeeeeeee eee eeeeee eeeeeeee ee eee eeeeeeeeeeeeee eeeeeee eeee eee eeee ee eeeeeeee e eeeeee eeee e eeeee eeeeeeeee eeeee. Meeeee 88 eee eee eee eeeeee eeeeee ee eee eeeeeeeeeeeeeeeee eeeee eee eeeeeeeee ee eeeee ee eee eeeeeeeeee eeeee ee eeeeee 88. Mee eeeeee eeeeee eeee ee eeeeeeeee eeee ee eeeeeeeeeeeeeeeeeeeee ee eee eeeeeeeeeee ee M-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeeee eeeeee 88. Meeeee 88 eeee eee eee eeeeeeeeeeee eeeeee ee eeeeee 88, eeeee eeeeee eeeeeee e eeeeeeeeeeeeeee eeeeeeeeee eeeeeeeeeee eeeeeee eee eeeeeeee/eeeeeeeeee eeeeeeeeeeee ee ee eeeeee eee eee eeeeeeee.

Meeeee 88 ee eeeeee ee eeeeeeeee eeeeeeee eee eee eeeeeeeeeee ee M-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee (Meeee 8). Mee eeeeee eeeeee ee eeeeee 88 eeeeeee eeeeeeeeee eeeeee eeeeeeeee ee eeeeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeee eee eee eeeeeeeeeee ee M-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee. Meeeee 88, eeeeeee eee eeeeee eeeeee, eeeeeeee eeee eeeeeeeeeeeeeeeeeeee eee eee eeeeeeeeeee ee eeee eeeeeee ee eeee eeeee. Mee eeeeee eeeeee eeeee eeeeee eeeeeeeee eeeee eeeeeeeee eeeee eeeeeeeeee eeeee 88, eee ee eeee eeeeee eeeee eeeeeeeeee eeeee 88 (Meeeee 88). Meeeeee, eeeeee 88 eeeeeeee eeeee eeeeeeeeeeeeeeeeeeee eee eee eeeeeeeeeee ee eee-eeeeeee eeee 88 eeee. Mee eeeeee eeeeee eeeeeeeeee eeeeee eee eeeeeeeeee eeeeeeeeee eeeeeee eee eeeeeeeeeeee eeeeee eee eee eeeeeeee eeeeeeeeeeee ee eee eeeeee. Meee eeeeeeeeee ee eeeeeeeeeeee eeeeee ee eeeeee eeeeeeeeee eeeeee (e.e., 88), eeeeeee eeeee eeeeeeeeeee eeee eeeee eeeeeeeeee eeeeee. Mee eeeeeeee ee eeeeeeeeee eeeeee eee eeeeeeee ee eeeeeeeeeeeeeeeeee, eee ee eeee eeeee (8-eeeeeeeeeeeeeeeee eee 8-eeeeeeeee-8-eeeeeeeeeeee) eeee eeeee eee eeeeeeee eeeeeeeeee ee eee eeeee eeeeeee.

Meeee 8 Meeeeeee Meeeeeeeee Meeeeeeeeee Meeeeee eee Meeeeeeeeeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeeee eeee Meeeeeeee Meeeeeeeeeee ee eee Meeeeeeeeeee Meee[‌88‌]

Meeeeeee Meeeeeee Meeeee Meeeee (eee%) Meeeeeeeee Meeeeee ee (%) Mee
88 (88) MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MeMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 88e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 8°M, 88e 88 [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88e [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88e [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88e [‌88‌]
88 (88) MMM/MM8(MMe)8 (8:8), ee eeeeee (eM8.8), 88°M, 8e 88e [‌88‌]

e ()-Meeeeeeeee.

e (+)-Meeeeeeeee.

Meeeee 88 Meeee eee Meeeee Meeeeeeeee Meeeee eee eee Meeeeeeeeee eeee e Meeeeeeeeeee-Meeeeeee Meeeeeeeeeee-Meeeeee Meeeee Meeeeee eee-Meeeeeee Meeeeeeeeeee ee eee Meeeeeeeee Meee[‌88‌]

Mee eeeeeeeeee eee eeeeee eeeeeeeeee ee ee eeeeee eeee eeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeeeeeeee ee eee eeeeeeeeeee. Meeeeeee eee eeeeee eeeeee eee eeeeeeeeee eeeeeeeeee eee eeeeeeeeeee eeeeeee eee eeeeeee eeeeeeeee eeeeeeee ee eee eeeeeeeeeee eeee eeeeee eeeeeee. Mee eeeeeeeeeee ee eeeeeeeeeeeee eee eeee eeeeeee eeee eeeeeee 88, 88, eee 88.[‌888‌] Mee eeeeeeeeeeeeeeeeeeee eee eeeeeeeee eeee eee eee eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeeeeee eeeee eeeeeee 88 eee 88 (Meeee 8). Mee eeeeeeeee eeeeeeeeeeeeee eee ee eeeeeeeee eeee eeeeee α-eeeeeeeeeee eeeeeee eeeee eeeeee eeeeeee-eeeeeee eeeeeeeeee. Meeeeeeeeeeeeeee eee 8,8-eeeeeeeeeeeee eeeeeeeeeeeee eeeeeeeee eeee eeee eeeeeee. Me eeeeeee eeee eeeeeeee eee ee eeeeeeeeee ee eeeeeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeeee eeee eee eeeeee eeeeeeeeeeee eee eee eeeeeeee eeeeeeee.

Meeee 8 Meeeeeee Meeeeeeeee Meeeeeeeeee Meeeeee eee Meeeeeeeeeeee[‌888‌]

Meeeeeee Meeeeeee Meeeee Meeeee (eee%) Meeeeee Meeee (%) ee (%) Meeeee Mee
88 (88) 88 88 (+) [‌888‌]
88M8M (88) 88 88 (+) [‌888‌]
88 (88) 88 88 (+) [‌888‌]
88 (88) 88 88 ()-(M,M) [‌888‌]
88M8M (88) 88 88 ()-(M,M) [‌888‌]
88 (88) 88 88 (+)-(M,M) [‌888‌]
88 (88) 88 88 (+) [‌888‌]
88M8M (88) 88 88 (+) [‌888‌]
88 (88) 88 88 (+) [‌888‌]
88 (88) 88 88 () [‌888‌]
88M8M (88) 88 88 () [‌888‌]
88 (88) 88 88 () [‌888‌]
88 (88) 88 88 (+) [‌888‌]
88M8M (88) 88 88 (+) [‌888‌]
88 (88) 88 88 (+) [‌888‌]
88 (88) 88 88 (+)-(M,M) [‌888‌]
88M8M (88) 88 88e (+)-(M,M) [‌888‌]
88 (88) 88 8 (+)-(M,M) [‌888‌]

e Mee eeeeeee eee eeeeeeeeeeee eeeeeeeeeee eeee (M)-8-eeeeeeeeeeee-8-eee eeee 88% ee.

Meeeeeeeeeee Meeeeeeee

eeeee-8-Meeeee-8-eeeeeeeeeeeee (88, M8=Me; M8=M; M8=Me); Meeeeee Meeeeeeee Meeee Meeeee 88 ee Meeeeeee eee Meeee ee Meeeeee:[‌88‌]

Me e eeee ee (M)-8-eeeeeeeeee-8-eee (88, M8=Me; M8=M; M8=Me; 8.888e, 8.8eeee) ee MeMM/MM8(MMe)8 (8:8; 88eM) eeee eeeee, eeee eeeeeeee, e eeeeee eeee eeeeeeeeee ee 8.88M Me8M8M888M8M ee 8×888 M ee Me8eeee (88eM), Me8MMMM8 (88ee, 8.88eeee), eee eeeeee 88 (8.8888e, 8.88eeee). M MeMe/eee eeee eee eeee ee eeee eee eeeeeee ee eeeee 88°M (eeeeee). M eeee ee Meeee (8.88e, 8.88eeee) ee 8×888 M ee Me8eeee (8.8eM) eee e eeee ee M8MM8 (8.8e, 8.8eeee) ee M8M (8.8eM) eeee eeeee eeeeeeee eeeeeeeeee eee eeeeeeeeeeeeee eeee e eeeeee ee 8e eee e eeeeeee eeee. Meee eeeeeeeeee ee eeeeeeee, eee eeeeeeee eee eeeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeee eee M8M. Mee eeeeeee eee eeeeeeeee eeee eeeeeee (8×88eM) eee eee eeeeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee eeeeeeee eeee 8% Me8M ee eeeeeee, eeeeeee/Me8M 8:8 ee 88:8) ee eeeeee e eeeeeeeee eeeeee; eeeee: 8.888e (88%); 88% ee.

eeeee-8-Meeeee-8-eeeeeeeeeeeee (88, M8=Me; M8=M; M8=Me); Meeeeee Meeeeeeee Meeee Meeeee 88 ee Meeeeeee eee Meeee ee Meeeeee:[‌88‌]

(M)-8-Meeeeeeeee-8-eee (88, M8=Me; M8=M; M8=Me; 8.888e, 8.88eeee), eeeeee 88M8M (8.888e, 8.888eeee), eee Me8MMMM8 (8.88e, 8.88eeee) eeee eeeeeeeee ee MeMM/MM8(MMe)8 (8:8; 8eM). M eM8.8 eeeeee eeee ee 8.88M ee Me8MMM8 eee 8.88M ee MM8MM8 (8eM) eee eeeee ee eee eeeeeee eeee eeeeeeee. Meee eeeeeee ee 8°M, e 8.888M eeee ee Meeee ee 8×888 M ee Me8eeee (8.8eM, 8.8eeee ee Meeee) eee 8.88M M8MM8 ee 8×888 M ee Me8eeee (8.8eM, 8.8eeee ee M8MM8) eeee eeeee eeeeeeee eeeeeeeeeeeeee eee eeeeeeeeee eeee 8e eee eeeeeee eeee. Meeee eee eeeeeeeeee ee eeeeeeee, eee eeeeeeee eee eeeeeeee ee eeeeeeee ee eeeeeee eee eeeeeeeee eeee eeeeeee. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee eeeeeeee eeee 8% Me8M ee eeeeeee eeeeeee, eeeeeee/Me8M 8:8 ee 88:8) ee eeee e eeeeeeeee eee; eeeee: 8.888e (88%); 88% ee.

eeeee-8,8-Meeeeeeeeeeeeee (88); Meeeeee Meeeeeeee Meeee Meeeee 88 ee Meeeeeee eee Meeeeeee Meeeeeee/Meeeeeeeeeee ee Meeeeee:[‌88‌]

(M)-Meeeeeee (88; 8.888e, 8.8eeee) eee eeeeee 88 (8.8888e, 8.88eeee) eeee eeeeeeeee ee MeMM/MM8(MMe)8 (8:8; 8.8eM). M 8.8M eeee ee M8MM8 ee 8×888 M ee Me8eeee (8.8eM) eee eeeee ee eee eeeeeee eeeeeeee ee eee eeeeeeee ee 88% M8M8 (8.8eM, 8.8eeee) ee 8°M. Meeee eeeeeeee ee 8°M eee 88e eee ee ee eee ee eeeeeeeeee 88e, eee eeeeeee eee eeeeeeeee eeee eeeeeee. Mee eeeeeeee eeee eeeeee eeee 8M ee Me8M8M8 eee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee eeeeeeee eeee 8% Me8M ee eeeeeee, eeeeeee/Me8M 88:8) ee eeeeee e eeeee eeeee; eeeee: 8.888e (88%); 88% ee.

eee-8-Meeeee-8-eeeeeeeeeeeee (88); Meeeeee Meeeeeeee Meeee Meeeee 88 ee Meeeeeee eee Meeee ee Meeeeee:[‌88‌]

(M)-8-Meeeeeeeee-8-eee (88; 8.888e, 8.8eeee) eee eeeeee 88 (8.888e, 8.888eeee) eeee eeeeeeeee ee MMM/MM8(MMe)8 (8:8; 8.8eM). M eM8.8 eeeeee eeee eeeeeeeeee ee 8.8M M8MM8/MeMM ee 8×888 M ee Me8eeee (8eM) eee Me8MMMM8 (8.8888e, 8.88eeee) eeee eeeee ee eee eeeeeee eeee eeeeeeee. Mee eeeeeee eee eeeeee ee eeeee 88°M (eeee eeeeeeeeeee) eeeee e MeMe/eee eeee, eee eeee e 8.88M eeee ee Meeee ee 8×88 8 M ee Me8eeee (8.8eM, 8.88eeee ee Meeee) eee 8.88M M8MM8 ee 8×888 M ee Me8eeee (8.8eM, 8.88eeee ee M8MM8) eeee eeeee eeeeeeee eeeeeeeeee eee eeeeeeeeeeeeee eeee e eeeeee ee 8.8e eee e eeeeeee eeee. Mee eeeeeeee eee eeee eeeeeeee ee eee eeeeeeee ee eeeeeee eee eeeeeeeee eeee eeeeeee. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee eeeeeeee eeee 8% Me8M ee eeeeeee, eeeeeee/Me8M 8:8 ee 88:8) ee eeee e eeeeeeeee eeeeee; eeeee: 8.888e (88%); 88% ee.

8,8-Meeeeeee-8,8e-eeeeeee-8eM-eeeeeee[8,8-e]-8-eeeeeeeeee (88); Meeeeee Meeeeeeee Meeee Meeeee 88 ee Meeeeeee eee Meeee ee Meeeeee:[‌88‌]

8,8-Meeeeeee-8-eeeeeeeeee (88; 8.888e, 8.88eeee), Me8MMMM8 (8.888e, 8.888eeee), eee eeeeee 88 (8.888e, 8.88eeee) eeee eeeeeeeee ee MMM/MM8(MMe)8 (8:8; 8.8eM). Meeee eee eeee eee eeee eeeeeee ee ee eee 88eee, e eM8.8 eeeeee eeee eeeeeeeeee ee 8.8M M8MM8/MeMM ee 8×888 M ee Me8eeee (8.8eM) eee eeeee. Mee eeeeeee eee eeeeeee ee ee eee ee eeeeeeeeee 88eee, eee eee eeee eeeeee eeeee ee eee eeee (8°M). Me eeee eeeee, 8.888M Meeee ee 8×888 M ee Me8eeee (8.88eM, 8.88eeee ee Meeee) eee e 8.88M eeee ee M8MM8 ee 8×888 M ee Me8eeee (8.88eM, 8.88eeee ee M8MM8) eeee eeeee eeeeeeeeeeeeee eee eeeeeeeeee eeee 8e eee e eeeeeee eeee. Mee eeeeeee eee eeee eeeeeeee ee eee eeeeeeee ee Me8M, eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee eeeeeeee eeee 8% Me8M) ee eeee eee eeeeeee eeeeeee.

8,8-Meeeeeee-8-eeeeeeeeeeeee (88); Meeeeee Meeeeeeee Meeee Meeeee 88 ee Meeeeeee eee M8M8/MeMM ee Meeeeee:[‌888‌]

M eeeeeee ee 8-eeeeee-8-eeeeeeeeee-8-eee (88; 8.888e, 8.88eeee) eee eeeeee 88 (8.888e, 8.88eeee) eeeeeeeee ee MeMM (8.8eM) eee eeeeee ee 8°M eeee ee eee eeee. Me eee eeee eeee eeeee MeMM (8.88eM, 8.8eeee) eee 8.88M M8MM8 ee 8×888 M ee Me8eeee (8.8eM, 8.8eeee M8MM8), eeeeeeee ee 88% M8M8 (8.88eM, 8.8eeee) eeee eeeeeeee eeeeeeee ee 8°M. Mee eeeeeee eee eeeeeee ee 8°M eee 88e, eee eeee eeeeeeee eee eeeeeeeee eeee eeeeeeeee eeeee. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M eee eee. ee Me8M8M8, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee eeeeeeee eeee 8% Me8M ee eeeeeeeee eeeee, eeeeeeeee eeeee) ee eeee e eeeeeeeee eee; eeeee: 8.888e (88%); 88% ee.

References


Cookie-Einstellungen