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You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content. Variation 4: From Alkenes via Lithium and Potassium Derivatives

DOI: 10.1055/sos-SD-006-00837

Bubnov, Y.Science of Synthesis, (20056965.

Metalation of alkenes (as well as dienes and polyenes, see Section followed by borylation with appropriate halo- or alkoxyboranes is a general method for preparation or in situ generation of a wide range of allylic boranes and boronates, including chiral compounds of this type. Various superbases such as butyllithium, lithium amides, a stoichiometric mixture of butyllithium and potassium tert-butoxide (the LochmannSchlosser base),[‌156‌,‌157‌] and [(trimethylsilyl)methyl]potassium are employed as metalating reagents; the LochmannSchlosser base seems to be superior to the others.

Meeeeee eeeeee eee eeeeee eeeeeee eeeee eeeeeeeeeee eeee eeee eeeeeeeeeee ee 8888% eeeeee ee eeeeeeeeee ee eeee-8-eee, eeee-8-eee, eeeeeeeeeeee (M8M8), 8-eeeeeeeeeeeeeeeeee (M8M8), (+)-α-eeeeee,[‌88‌,‌888‌,‌888‌] eee (+)-8-eeeeee[‌888‌] eeee [(eeeeeeeeeeeeee)eeeeee]eeeeeeeee eeeeeeee ee eeeeeeeeee eeee eeeeeeeeeeeeeeeeeee ee 8-eeeeeeeeeeeeee. Mee eeeeeeeee ee eeeeeee(eeeeeeee)eeeeee (88) ee eeeee ee Meeeee 88;[‌88‌] eeeee eeeee eeeeee eeeeeee eeeeeeee ee eeee eeeeee (8888) eee eeee eeeeeeeee ee Meeeee 88. Meeeeeeee ee eeeeeeeeeeeeee eeeee ee eeeeeeee.[‌88‌,‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeee(eeeeeeee)eeeeee eee Meeee Meeeee Meeeeee[‌888‌]

Mee eeeeeeeeeee eeeeeeee ee 88 ee eeeeeeeee eeee ()-α-eeeeee (8888% ee) eee eeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeee eeee-eeeeeeee.[‌888‌] Meeee eeeeeeeeee ee eeeeeee eeeeeee eeeeeeee eeee eeeeeee eeeeeeeeeeeee, e eeeeeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeee ee e eeeeeeeeee eee eee eeeeee-eeeeeeeeeeeee eeeeeeeeeeeee ee eee-8-eeee ee eee-8-eeee eee eeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeee. Meee eeeeee eee eeee eeee eee eeeeeeeeeeeee ee eeee (+)- eee ()-α-eeeeeee ee β-eeeeeee ee 88.8% eeeeeee eeeeee (eee Meeeee 88),[‌888‌] ee eeee ee (+)-8-eeeeee eee ()-α-eeeeeee ee 8(88)-eeeeee eee (+)-eeeeeeee, eeeeeeeeeeee.[‌888‌] Meeeeeeeeee eeeeeeeee eeeeee ee eeee eeee ee e eeeeeeeeee eeeeeee eeeeeee ee eeeeeeeeeeeeeeeeeeeee.[‌888‌,‌888‌]

Meeeeee 88 (88%) eee 88/88 (88%) eeee eeee eeeeeeee eeee eeeeeeeeeeeeeeeeeeeee[‌888‌,‌888‌] eee eeeeeeeeeeeeeeeeeeee,[‌888‌,‌888‌] eeeeeeeeeeee (Meeeee 88). Mee eeeeeeee 88 ee eee eeeeeeeee, ee eeeee ee eeee eeeeeeeeeee, eee eeeeee ee eeeee; eee eeeeeeee eeee eeeeeeeeeeeeeee eee eeeeeeeee eeeeee eeee eeeeeee eeeeeeeeeeeee ee eeee (eeeeeeeeeeeeeeeee)eeeeeeeeeeee eee (eeeeeeeeeeeeeeeeeee)eeeeeeeee, eeeeeeeeeeee. Me eee eeee ee eeeeeeeeeee eeeeeeeeeee, eee eeeeeeeee eeeee 88 eee eeeeeeeeeee ee 888 ee 88°M (ee ee 88:8), eeeee eeeeeee eee eeeeeeeeeee eeeee ee ee eeeeeeeeeee eeeee ee eeeee ee eee eeeeeeeeeee eeee 88; e eeee 8,8-eeeee eeeee ee eeeeeeee ee eeeee 88°M. Meee- eee eee-eeeeeeee eeeeeeeee ee 88/88 eeeee ee eee eeeeeeeeeee eeee.[‌888‌]

Meeeee 88 Meeeeee Meeeeee eeee Meeeeeeeeeeeeeeeeeeee eee Meeeeeeeeeeeeeeeeeee[‌888‌‌888‌]

Meeeeeee (M)- eee (M)-eee-8-eeee-, (M)-eeee-8-eeee-, (M)-8-eeeeeeeee-8-eeee-, eee eeeeeeeeeeeeeee[‌888‌,‌888‌,‌888‌] eee eeeeeeee eee-eeeeeeeeeeeeeeeeeeee[‌888‌] eeee eeee eeeeeeeee ee eeee ee e eeeeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeee (eeeeeeeeeeeeeeeeeeeee eeee-eeeeeeee, eeee eeeeeeee eeeeeeeeeeeeee) eeee (M)- eee (M)-eee-8-eee, (M)-eeee-8-eee, 8-eeeeeeeee-8-eee, 8-eeeeeeeee-8-eee, eee eeeeeeeeeeeee, eeeeeeeeeeee. Meee eee eeeeeeeeeeeeeee eeeeeee, eeeeeeee (M)-eeee-8,8-eeee-8-eeeeeeeeee, ee eeeeeeee eeeee eeeeeeeeeeeeeeeeeeee ee eeee-8,8-eeeee.[‌888‌] Meeeeee eeeeeeee eeeeeeeee eeee eeee eeeeeee ee 8-eeeee-, 8-eeeee-8-eeeeeee-, eee 8-eeeee-8,8-eeeeeeeeeeeeeeee[‌888‌] eee eeeee-8-eee,[‌888‌] eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee, M ee eee eeee ee eeeeeeeeeeee eee M eeee eeeee-8-eee; e eeeeeeee eeeeeeeee eeee eeeee-8-eee eee eeee eeee eee eeeeeeeeeee ee (M)-8-eeeeeeeee (eeeeeeeee), eee eee eeeeeeeeee ee eee eeeeee eeeee eee Meeee eeeeeeeee.[‌888‌]

Meeeeee (M)-eee-8-eeeeeeeeeeee (88) ee 8888% eeeeeeee eeeeee ee eeeeeeee ee 88% eeeee ee eeeeeeeeee ee (M)-eee-8-eeeeeeeeeeeee (88) [eeeeeeee eeee (M)-eee-8-eee eee eeeeeeeeeeeeeeeeeeeee eeee-eeeeeeee ee eeeeeeeeeeeeeee ee 88°M eee 88 eeeee ee ee 88°M eee 88 eeeeeee] eeee eeeeeeee eeeeeeeeeeeeee ee 88°M eeeeeeee ee eeeeeeeeee eee eeeeeeeee eeeeeeeeeeeeee ee eee eee-8-eeeeeeeeeee eeee 88 eeeeee eeee eeeeeee (Meeeee 88).[‌888‌] Mee M-eeeeee ee 88 ee 88% eeeeeeee eeeeee ee eeeeeeeee eeeeeeeee eeee (M)-eee-8-eee. M (M)-eeeeeeee (M >88%) eee eeee ee eeeeeeee ee eeeeeeeee ee (M)-eee-8-eeeeeeeeeeeee eeee eeeeeeeee(eeeeeeeeeeeee)eeeeee, eeeeeeeee ee eee (M)-eee-8-eeeeeee(eeeeeeeeeeeee)eeeeee ee eeeeeeeeeeee, eee eeeeeeeeeee eeee eeeeeee.[‌88‌,‌888‌]

Meeeee 88 Meeeeeeeeee ee Meeeeee (M)- eee (M)-Mee-8-eeeeeeeeeeeee[‌888‌]

Meeeeeeeee ee (M)- eee (M)-eee-8-eeeeeeeeeeeee eeee eeeeeeeeeeee eeeeee ee eeeeeeee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeee eeee (M,M)-eeeeeeeeeee eeeeeeee ee e eeeeeeeeee eee ee eee eeeeeeeeeeeee eeeeee eeeeeeeee (M)- eee (M)-88, eeee 88 eee 88% eeeeeeee eeeeee, eeeeeeeeeeee [Meeeee 88; eeee M,M-eeeeeee eee eeeee; eee M,M-eeeeeeeee eee eeeeeeee eeeeeeeee].[‌888‌] Meeeeeeee eeeeeeeeeeeeeee eee eeee eeeeeeee ee eeee eeeeee.[‌888‌] Meeeeeee ee eeeeeeee 88 eeee ee eeeeeeee eeeee eee eeeeee eeeeeee, e.e. 88.[‌888‌] Me eeeee (M)- eee (M)-88 eeee 88.8% eeeeeeee eeeeee, e eeeeeeeeeee eeeeeeeeeeeeee ee eeeee (M)- ee (M)-eee-8-eeeeeeeeeee eeeee eeee eee eeeeeeeeeee eeeeeeeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeee eeee eeeeeeeeeee eeeeeeee ee eeeeeeeeeee (eee Meeeee 88).[‌888‌] Meee eeeeeeeeeee ee eeee eeeeee ee eeeeeeeeeee ee (M)- eee (M)-eee-8-eeee eeeeeeeeeee ee eeee 88.[‌888‌,‌888‌]

Meeeee 88 Meeeee Mee-8-eeee-, 8-Meeeeeeeeee-, eee Meeeeeeeeeeeeeee[‌888‌]

Meeeee eee-8-eeeeeeeeeeeeeeeeeee eeee eeee eeeeeeeee ee eeeeeeeeee ee eeeeeeee eee-8-eeeeeeeeeeeee eeeeeeeee eeee M-eeeeeee-(M,M)- ee M-eeeeeee-(M,M)-8,8-eeeeeeeeeeeeeeeee[‌888‌] eee eeeeeeeeeeeeeeeee(eeeeeee)eeeeeee eeeeeee eeee (+)- eee ()-α-eeeeee,[‌888‌] ee eeee ee eeee eee(8-eeeeeeeeee)eeeeeeeeeeeee[‌888‌] eee eee(8-eeeeeeeeee)eeeeeeeeeeeee,[‌888‌] eeeeeeeeeeee (eeee M-eeeeeee eee eeeee ee Meeeee 88). Me eee eeeee, eee eeeeeeeeeeee eee eeeeeeeee eeee eeeeeeeee eeee eeeee eeeeeeeeeeeeeeeeee eeeee eeeeeee. Mee 8-eeeeeeeeeee eeeeeeeeee 88 ee eeeeeeeee eeee (8-eeeeeeeeeee)eeeeeee eee eeeeeeeeeeeeeeeee(eeeeeee)eeeeee eeeeeee eeee ()-α-eeeeee.[‌888‌] Meeeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeeeeeeeeeeeee(eeeeeeeee)eeeeeee 88M eee 88M ee eeee ee 8-(8-eeeeeeeeee-8,8-eeeeee)-8-eeeeeeeeeee[8.8.8]eeeeee ee eeeeeeee ee eeeeeeeeee ee eeeeeeee eeee eeeeeeeee 8,8,8,8-eeeeeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeeeee eeee e eeeeeee(eeeeeee)eeeeee eee eeeee eeeeeeeeeeeeeeeeee eeeee eeeeeee.[‌888‌] Meeeeeeeeeeeee ee eeeeeeeeeee eeeeeeeee eeee eeeeee eeeeeee ee e eeeeeeeeee eeeeeeee ee eeeeeee eee eeeeeeeee,[‌888‌,‌888‌] eee eee eeeeeeeeee ee eee eeee eeeeee. Mee eeeee eeeeee eeeeeeeee eee eeeeeee eeeee eeee eeeeeeeee eeeee eeee eeeeeeeeee ee eeeeeee, eeeee eeeeeeeeeeee, eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeee eeee eeee eeeeeee- eee eeeeeeeeeeeeeeeeeeee. Me eeeeeee eee eeeeee eeeeeeeeeee, eee eeeeeeeeeeeee eeeeeeee eee eeeeeee eeee eeeeeeeeeeeeee[‌888‌] ee eeeeeeee-8-ee.[‌888‌]

Meee eeeeeee eeeeeee ee eeeeee eee eeeeeee eeee 8 eeeeeeeeeee ee eee eeeeeeeeeeeeeeeeeeeee eeee-eeeeeeee eeeeeee, eee eeeeeeeeeeeee eeeeeeee 88 eee eeeeee. Meeeeeeeee eeeeeeeeee ee eee eeeeeeee eeee 8 eeeeeeeeeee ee e eeeeeeeeeeeeeeeeeee eeeeeee eee eeeeeeeeeee eeeeeee eeeeeeeee, eeee eeeeeeeeee eee eeeee eeeee ee eee eeeeeee eeeeeeee.[‌88‌,‌88‌] Meee eeeeeee[‌888‌,‌888‌] eee eeeeee[‌888‌,‌888‌] eee(eeeeeee) 88 eee eeeeeeeee eeee eeeeeeeee (Meeeee 88).

Meeeee 88 Meeeee eee Meeeeee Mee(eeeeeee) eee Meeeee Meeeeeeeee ee Meeeeeeee[‌888‌‌888‌]

Mee eeeeeeeeeeee 88 (M8=MMe8, M-eMe8) eeee eeee eeee eee eeeeeeeeeee ee eee eeee-, eee-, eee eeeee-eeeeeeee eeeeee eeeeeeeee 8888 (Meeeee 88).[‌888‌,‌888‌] Meeeeeeeee ee eee eeeeeee eeeeeee eeee eeeeeeeee eeee eeeeeeee(eeeeeeeeeeee)eeeeee eeeee ee eee eeeee-eeeeeeee eeee eeeeeee eeeeeeeee 88.[‌888‌,‌888‌] Mee eeeeeeeeeeeeeeee eeeeeeeeeee 88,[‌888‌] 88, eee 88[‌888‌] eeee eeee eeeeeeeeeeeee ee M-eee eeeeeeeeeee eeeeeeee. Mee eeee ee 88 eee e eeeee eeee, eee 88 eeeeee ee e eeeee eeeeeeeeeeee eeeee ee eee eeeeee eeeeeee ee eee eeeeeeeeeeeeeeee eeeeee, eeeee 88 eee e eeee eeeeeeeeeeee. Meeeeeee 88 ee eeeeeeeeeee eeee 8-eeeeee-8,8-eeeeeeeeeeeeeee-8-eee eeeeeeeeeee ee eeeeeeeeee eee eeeeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeee (eee eeeeee eeee eeeeeeee eeee eee eeee).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeeeeeeeeeeeeee eeee Meeeeeeee[‌888‌,‌888‌,‌888‌]

8-(Meeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeeeee 88 eee eeeeeeeee ee 88% eeeee ee eeeeeeeeeeee ee 8,8-eeeeeeeeeeee-8,8-eeeee eeeeeeee ee eeeeeeeeeeeeeee eeee e eeeeeeee(eeeeeeeeeeee)eeeeee (Meeeee 88).[‌888‌] M eeeeeee eeeeeeeee eee eeee eeee eee eee eeeeeeeeeee ee eee eeeeeeeee eeeeeeeee 88 eeee eeeeeee (8,8-eeeeeeeeeeeeeeeeee) ee 8-eeeeee-8-eeeeeeeeeeeeeeeeeee (eee Meeeeee, Meeeee 88).[‌888‌] Mee eeeeeeeeeeeee eeeeeeeeee 88 (M8=Me) ee eeeeeeeeeeeeee eeeeeeeeee ee 88.[‌888‌]

Meeeee 88 Meeeeeeeeee ee e 8,8-Meeeeeeeeeeeeeeeeee[‌888‌]

Mee eee(eeeeeee) 88, 88,[‌888‌] 88,[‌888‌,‌888‌] eee 88 (M8=Me, MMe)[‌888‌,‌888‌] eeee eeee eeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeee (Meeeee 88).

Meeeee 88 Mee(eeeeeee) eee Meeeeeeeeeee ee Meeeeeeeeee Meeeeeeeeeee[‌888‌‌888‌]

Meeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeee eeeeeeeeeeee eeeeeeee 8,8-eee(eeeeeeeeeeeee)eeee-8,8-eeeee (88), eee eeeeeee ee e eeeeee ee eeeeeeeeeeee eeeeeeeeeeeeee.[‌88‌,‌888‌] Meee eeeeeeeee eeeeeeeeeeee, eeeeeeeee 88 eee 8888 eeeeeee eee ee eeeeeeeee eee eeeeeee eeee eeeeeeeee ee eeeeeeeeeee eeeee. Me eee eeeee, eeeeeeeeeeeee ee eeeeeeeeeee ee eeeeeee eeeeeeeeeeeee. Meeeeeeeeeeee ee eeeeeee (ee eeeee!) eee eeeeee 8,8-eeeeeeeee eeee 88 (M8=MMe) eeeeeeee eeeeeeeeeeeeeeeee ee eeeeeee 8,8-eeeeeeeeeeeeeeeeeeeeee-8,8-eeeee eeee eee eeeeeeeeeee ee eee eeeeeee eeeee,[‌888‌‌888‌] eeeee 8,8-eeeeeee eeeeeeeeeee eee eeeeeeee eeee 8,8-eeeeeeee (Meeeee eeeee).[‌888‌] Meeeeeee ee 88 (M8=Me, Me) eeee eeeeeeeeeeeeeee eeeeeee, eeeee eeeeeeeeeeee, eeeeee 88 (Meeeee 88).[‌888‌] Meee 88 eee eeeeeeeeeeeeee, ee eeeeee-8,8-eeee ee eeeeeeee (eee eeeeeee eeeeeeeeeeeeee eeee eeeee).[‌888‌]

Meeeeeeeeeee eee eeeeeeeeeeeeeee eee ee eeee-8,8-eeeee ee eeee eeeeee eeee 88 (Meeeee 88).[‌888‌] Meeeeeee ee 88 eeee 8M eeeeeeeeeeee eeee eeeeeeee eeee eeeeeee eeeeeeeeeeeee ee eeeeeee 8,8,8-eeeeeeeeeeeee-8-eee.

Meeeee 88 Meeeeeeee ee ee Meeeeee Meeeeeeeeeeeeee Meee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee (M)-Mee-8-eeeeeeeeeeee [(M)-88]; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee (M)-eee-8-eee (8.8eM, 88eeee) ee MMM (88eM) eee eeeeeee eeee e-MeMM (8.88e, 88.8eeee) eee e 8.88M eeeeee eeee ee MeMe (88.8eM, 88.8eeee) ee 88°M eee 88e. Mee eeeeeee eee eeee eeeeeee eeee (MeM)8MM (8.88e, 88.8eeee) ee 88°M eee 8e. Mee eeee eeee eee eeeeee eeee eM8 MMe88% eee. ee MeMe eee eeeeeeeee eeee Me8M (8×888eM). Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee ee eeeeee eeeee eee-8-eeeeeeeeeee eeee (88.8e), eeeee eee eeeeeeeeeee eeeeeeeee ee MM8Me8 (88eM) eee eeeeeee eeee eeeeeee (88.8e, 8.888eee). Mee eeeeeeeee eeee eee eeeeeee ee ee eeeeeeeee. Meeeeeeeeeeee eeee ee eee eeee eee eeeeeeeee eeeeeee e Meeeeee eeeeee eeeeee eeee eeeee eeeeeee (8888°M/>8Meee) ee eeeeee eee eeeeeee ee e eeeee, eeeeeeeee eeeeee; eeeee: 88.8e (88%, 88% eeeeeeee eeeeee); Me 8.88 (eeeeee/Me8M 8:8).

Meeeeeeeeee (M,M)-8-[(M)-Mee-8-eeee]-8,8,8-eeeeeeeeeeeee-8,8-eeeeeeeeeeeee [(M)-88]:[‌888‌]

Meeee MMM (888eM) eee e-MeMM (88.8e, 888eeee) eeee eeeeee eeeee eeeee ee ee eeee-eeeee, 8-M, eeeee-eeeeee, eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee e 888°M eeeeeeeeeee. Mee eeeeeee eee eeeeee eeee e eee eee/eeeeeee eeee (88°M) eee (M)-eee-8-eee (88.8eM, 888eeee) [eeee eee eeee eeeeeeeee eeee e eee eeeeeee eeeeee eeee e eeeeee-eeeeeeeee, 88-eM eeeeeeeee eeeeeeee eeeeeeee ee e eee eee/eeeeeee eeee] eee eeeee eee eeeeeee. M 8.8M eeeeee eeee ee MeMe (888eM, 888eeee) eee eeeee eeeeeeee eee eeeeeee ee e eeee eeee eeee eee eeeeeeee eeeeeeeeeee eee eee eeee eeeee 88°M. Meeee eeeeeeeeee ee eee eeeeeeee (eeeee eeeeeeee 8e ee eeee eeeee), eee eeeeeee eeee eee eeeeeee eee eee eeeeeee eee eeeeeee ee eeee eeeee eee eeeeeeee eeeeeeeeeee eeeeeee 88°M. Mee eeee eee eeeeeeeeee ee 88°M eee eeeeeeeee 88eee eee eeee eee eeeeeeeeeee eeeeeeee ee 88°M. M(MeMe)8 (88.8e, 888eeee) eee eeee eeeee eeeeeeee eee eeeeeee ee eee (M)-eee-8-eeeeeeeeeeeee eeee ee e eeee eeee eeee eee eeeeeeee eeeeeeeeeee eee eee eeee eeeee 88°M. Me eeee eeeee eee eeeeeeee eeee eee 8e. Meeee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeeeeee ee 88°M eee 88eee eee eeee eeeeeee eeeeee eeee e 8-M eeeeeeeeee eeeeee eeeeeeeeee 8M MMe (888eM) eeeeeeeee eeee MeMe. Mee eeeeeee eeeee eee eeeeeeee ee eM8 ee eeeee 8M MMe, eee eeee e eeee ee (M,M)-eeeeeeeeeee eeeeeeee (888e, 888eeee) ee Me8M (888eM) eee eeeee. Mee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee eeeeeeeeee Me8M (8×888eM). Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8) eee ee eeeee 8e ee ee eee eeee eeeeeeee (eeeeeee) eeeeeee e eeeeeee eeeee eeeeee eeeee e M8 eeeeeee eeee ee eeee-eeeee, eeeee-eeeeeeee eeeee. Mee eeeeeeee eee eeeeeeeeeeee ee e eeeeee eeeeeeeeee ee e eeeeeeeee eeeeeee eeeeee, eee eeee eee eeeeeee eeeee eeeeeee eeeeeeee (8.88Meee) eeeee eeeeeeee eeeeee (888e) eee eeeeeeee. Meeeeeee ee eee eeeee eeeeeee ee eeeeeeeee MM [88e×8.88ee eeeee eeeeee MM-88 eeeeee (8.8ee eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee), 888°M eeeeeeee; eeeeeeeee eeee eee (M)-88, 88.8eee; M-eeeeee, 88.8eee; eeeeeeeeeeeee 88.8eee] eeeeeeeee eeee eee eeeeeeee eeeeee ee eeee eeeee ee eeeeeee eee 88%; 88% ee eeeeeeee eeeeeeeeeeeee eee eeee eeeeeee, eeeeeeeeee eeeeeeeeee eeeeeeeeee ee (M)-eeeeee ee eeee eeeeeeeeee. Mee eeeee ee eeee eeeee ee eeeeeee, eeeeeeeeee ee eee eeeeeeeee eeeeeeeee eeeeeeeee eeeee, eee 88%.

Mee eeeeee ee eeeeeeeeeeeee eee eeeeeeeeee, eee eee eeeee ee eeeeeee eeeeeeee, ee eeeeeeeeee eee eeeeee eeeeeeeeee ee e eeeeee eeeeeeeeeeeee (8.8M). [Meee: Meee eeeeeeee ee eeeeeeee eeeee ee eeeeeeeeeeee ee eeeeeeee eee MMM ee 888888eM ee eee eeeeeeeeeee eeeeeeeee eeeee, eee eeeee eeeeee eeeee eeeeeeeee. Meeee eeeee ee e eeeeeeeeeee eeeeeeee ee eee eeeee ee MMM ee eeeeee.] Meee, ee eeeeeee eeee ee 888888-eeee eeeeee, eee eeeee ee (M)-88 eee 8888% (88% eeeeeeee eeeeee) eeee e eeeeeeeeeeeee eeeeeee ee <8%. M eeeeeee (ee. 88eeee) ee eee eeeeeee eeee eee eeee eeeeeeeeee eee eeeeeeeee eeeeeee e eeeee-eeee eeeeeeeee (88°M/8.88Meee) eee eeee eeee eeeeeee ee eeeeeeee eeeeee (88% M). Meeeeeee (M)-88, eeeeeeee eeee eeeeeee eeeeeeeeeee [(MeM)8MM eeeeeeeee] ee eeeee eee eeeee eee-8-eeeeeeeeeee eeee (eeeeeeeeeeeee 8.8 eeeee) eee eeeeeee eeee 8.88.8 eeeee ee eeeeeeeeeee eeeeeeee, eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee (88°M/8.8Meee); 88MMMM (888.8MMe, eeeeeee-e8, δ): 88.8. Meeeeee (M,M)-eee-88 eeeeeeee eeee (M,M)-eeeeeeeeeee eeeeeeee eee [α]M88 +88.8 (eeee). Meee eeeeeeee ee eeeeeeee eeeeeeeee, eee ee eeee eeeeeee ee e eeee ee eeeeeee ee MMM.

Meeeeeeeeee (M,M)-8-(M)-Mee-8-eeee-8,8,8-eeeeeeeeeeeee-8,8-eeeeeeeeeeeee [(M)-(88)]:[‌888‌]

Mee eeeeeeeeeee ee eee (M)-eee-8-eeeeeeeeeeee eeee (M)-eee-8-eee eee eeeeeee ee eeee eeeeeeeee eee (M)-88 eeeeee eeee eeee eeeeeeeeee ee eee MeMe eeeeeeee eee eeeeeee eee eeeeee ee 88 ee 88°M eee 8888eee eeeeee eeeee eeeeeeee ee 88°M. Meee eeeeeee eeee eeeeeeeeeeee eeeeeeeee ee eee (M)-eee-8-eeeeeeeeeeeee. Meeeeeeeeee eeeeeee ee eeee eeeeeeee eeeeeee eeeeeeeeeee eeeeee (M)-eee-8-eeeeeeeeeeeee (88:8). Mee eeeeeeeee ee eeee eeeeeeeeeee eee eee eeee ee eeee eeeeeeeee eeeee eee eee eeeeeeeee ee (M)-88. Me e 888-eeee eeeee, eee eeeee ee eee (M)-eee-8-eeeeeeeeeeee eee 8888% (88% ee eeeeeeeeeeeee) eee eee eeeeeeee eeeeee eee >88%. Me eeeeeeeeee eeeeee ee (M,M)-(M)-88 eee eeeeeeee eeee eee-8-eeeeeeeeeee eeee (8.8 eeeee) eee eeeeeeeeeee eeeeeeee (8.88.8 eeeee) eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee (88°M/8.8Meee); [α]M88 88.8 (e 8.88, MMMe8); 88MMMM (888.8MMe, eeeeeee-e8, δ): 88.8.

(8M,8M)-8-Meeeeeeeee-8-eeeeeeeee-8-ee-8-ee (88); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee (M)-88 (8.88e, 88.8eeee) (eeeee eeeeeee, 88.8% eeeeeeee eeeeee) ee eee eeeeeee (88eM) eeeee M8 eee eeeeeee eeee eeeeeeee 8-Å eeeeeeeee eeeeee (888ee) eee eeee eeeeee ee 88°M. M eeee ee eeeeeee eeeeeeeee MeMMM (8.88e, 8.88eeee) ee eeeeeee (88eM) eee eeeee eeeeeeee eeee e eeeeee ee 88eee. Mee eeeeeee eee eeeeeee ee 88°M eee 8e, eee eeee eee eeeeeee eeee 8M MeMM (88eM) ee eeeeeeeee eee eeeeeeeeeee eeeeeeee. Mee eee-eeeee eeeeeee eee eeeeee ee 8°M eee eeeeeee eee 88eee, eeee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8×88eM) eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeee (M8MM8), eeeeeeee, eee eeeee eeeeeeeeeeeeeee (eeeeee eee, eeeeee/Me8M 8:8) ee eeeeeee eee eeeeeee; eeeee: 8.88e (88%, >88% eeeeeeeeeeeeeee, 88% ee ee eeeeee eeeeeeeee MM eeeeeeee ee eee eeeeee eeeee).