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19.5.9.2.1 Method 1: Addition without External Stereocontrol

DOI: 10.1055/sos-SD-019-00155

North, M.Science of Synthesis, (200419266.

Earlier work in this area has been reviewed.[‌26‌] By far the most common set of reagents for the formation of cyanohydrins from ketones is trimethylsilyl cyanide and catalytic zinc(II) iodide. These reagents will result in formation of cyanohydrin trimethylsilyl ethers from diaryl ketones,[‌209‌,‌210‌] alkyl aryl ketones,[‌209‌‌211‌] aliphatic ketones,[‌209‌,‌210‌,‌212‌] and benzoquinones.[‌213‌,‌214‌] In some cases, however, the use of potassium cyanide/18-crown-6 as an alternative catalyst has been recommended.[‌215‌] Zinc(II) iodide also catalyzes the addition of tert-butyldimethylsilyl cyanide and tert-butyldiphenylsilyl cyanide to even sterically hindered ketones, and is superior to the use of potassium cyanide/18-crown-6 as a catalyst in this respect.[‌216‌] The diastereoselective addition of trimethylsilyl cyanide (or dimethylsilyl dicyanide[‌217‌]) to β-hydroxy ketones has been investigated. The reaction was originally reported to be highly syn selective,[‌218‌] but later studies showed that the observed diastereoselectivity was actually largely due to diastereoselective hydrolysis of the anti-diastereomer during the reaction workup.[‌219‌] Despite this, it is still possible to obtain syn-β-hydroxy cyanohydrins with high diastereomeric excesses from this reaction, albeit in moderate yield.

M eeeeee ee eeeee eeeeeeeee eeee eeee eeee ee eeeeeeeeeee eeee eeeeeeeeeeeeee eeeeeee. Meeeeee eeeeeeeeeee ee eeeeeee eeeee ee eeeeeee eeeeeeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee eee eeeeeeee eeeeeee eeeeeeeeeeeeee eeeeeee eee eeeeee eeeeeee ee eeeee eeee eeeeeee, eeee eee eeeeee eeeeee eeeeeeeeeeee eeee eeeeeee.[‌888‌] Meeeeeeeeeee ee eeeeeee eeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeee eeeeeee eee e eeeeee eeee eeeeeee ee eeeeeeeee ee eee eeeeeeeeeee eeeeeeeeeeeeee eeeee ee 8888% eeeee.[‌88‌] Meeeeee eeeeeeeee eee eeeeeeeeee eeeeeee 88 (Meeeee 88) eeeeeeee eee eeeeeeee ee eeee eeeeeeeeeeeeee eeeeeee eee eeee-eeeeeeeeeeeeeeeeee eeeeeee ee eeeeeee. M eeee eeeee ee eeeeeeeeee eeee eeee eeeeeeee eeeee eeeeeee 8.888 eee 88eee% ee eee eeeeeeee, eee eeeeee ee 8888% eeee eeeeeeee eeee eeee eeeeeeeeee eeeeeeee eeeeeee. Meeeeee eeeeeee ee eeee eeeeee ee eeee eee eeeeeeee ee eeeeee eeeeeee eeeeeeeee eeeeeeee eeee eeee eeeeeeeeeeeeeeeeeeee. Mee eeeeeee, eeeeeee eeeee e 88:8 eeeee ee eee eeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeee eeeeee, eeeeee eee eeee eeeeeeeee eeeee eeee(MM) eeeeee eeeeeeeee eeeee e 88:88 eeeee ee eeeeeeeeeeeeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeee-, Meeeeee-, eee Meeeeeeeee-Meeee Meeeeeeee eee eee Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee Meeeeee[‌88‌,‌88‌,‌888‌]

Meeeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeeee (88) (Meeeee 88) ee e eeeeee eeeeee eeeeeeee eee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeee. Meeeeeeee eeeeee (8888%) eee eeeeeeee eeee eeeeeeeee eee eeeee eeee eeeeeee ee 88°M ee eeee eeee 8 eeee, eeeee eeee 8eee% ee eee eeeeeeee.[‌88‌] Meee eeeeeeee, eeeeeeeeeee eeee 88 (Meeeee 88) eee eeee eeee eeeee ee eeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee e eeeee ee eeeeeee ee 8888% eeeee. Mee eeeeeeeee eeeee ee eeee eeeeeeeeeee, eee eeeeeeee ee 8 eeee, eee eee eeeeeee ee eeeeeee eeeeeee e eeeeeeeeeee eeeeeee eeeeeee ee eeeee eee eeeeeeeeeee ee eeeeeeeeeee ee eee eeeeeeeeeeeeee eeeee.[‌88‌] Meeeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee eee eeee eeee ee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeeeee eee eeeee eeee eeeeeee, eee eeee 8eee% ee eee eeeeeeee ee eeeeeeee.[‌88‌] Mee eeeeeeee eeeeeee [M(MM)MM(MM8M8)8(MM)8](MeM8)8 eeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeeee eeeeeee 88°M eee eeee eeeeeeeeeee, ee eeee 8888% eeeeee ee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeee eeeeee.[‌88‌] Meeeeeeee(MMM) eeeeeee[‌88‌,‌888‌] eee eeeeeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeee[‌88‌] eeee eeeeeeee (88eee%) eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee e eeee eeeee ee eeeeeee. Meeeeeeee(MMM) eeeeeee eee eeee eeeee ee eeee eeee 8,8-eeeeeee eeee α,β-eeeeeeeeeee eeeeeee eee eeee eeeee eeee eeeeee eeeeeeeeee eeeeeee eeee ee eeeee 8-eeeeeeeeeeee. Meeeee(MMM) eeeeeee eee eeee eeeee ee ee e eeeeee eeeeeeeee eeeeeeee, eeee 8.88eee% eeeee eeeeeeee ee eeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee e eeeee ee eeeeee eeeeeeeeeeeeee eeeeeee, eeeeeeeeee eeeee eeeeeee eeeeeeeeeee ee eee α-eeeeeeee ee eee eeeeee.[‌888‌] Meeeee(MMM) eeeeeee eeee eeee eeeeeeee eee eeeeeeeeee Meeeeee eeeeeeee ee e eeeeeeeeeee (eeeeee ee eeeee) eee 8,8-eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee ee α,β-eeeeeeeeeee eeeeee.[‌888‌] Meeeeee(MMM) eeeeeee eee eeee eeee ee eeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeee eee eeeeeeeeeeeee, eee eeee 8eee% ee eee eeeeeeee eee eeeeeeee.[‌88‌] Meeeeeeeee eeeeeeeeee eee eeeeeeeeeee eeeeeeeeee eeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeee eee eeeeee-8-eee, eeee eee eeeeeeeeeee eeeeeeee eeeee eeee eeee eeeeee (88% eeeee ee eee eeeeeeeeeeee eeeeee eeeee 8.8 eeeee ee eeee eeeeeeeeeee eeeee 8eee% ee eee eeeeeeee).[‌88‌] Meeeeee eeeee eeeeeeeee eeee ee eeeeeeeeeeeeeee eeee, eeeeeee eeeeeeee, eee eeeeeeeeeeeeee eeee eeee eeee eeeeeeee ee eeeeeeeee eee eee eeeeeeeeeeeeeeeeeeeeeee ee eeeeeee.[‌88‌,‌88‌] Meeeeeeee-eeeeeeeee eeeeeeeee(MM) eeeeeeee eeeeeeeee eee eeee eeee eeee ee e eeeeeeeeeeeee eeeeeeee eee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeee. Meeeeeeee eeeeeee eee ee eeeeeeeee eeeeeeeeeeeeeee eeee 8888% eeeeee ee eeeeeeeeeee eeeeeeeeeeeeee eeeeee ee 8.888eeeee eeee eeeeeeeee eee eeeee eeee eeeeeee.[‌88‌] Mee eeeeeee M-eeeeee 88 eee 88 (Meeeee 88), eeee eeeeeeeee ee eeeeeeee(MM) eeeeeeeeeeee, eeee eeee eeeee ee eeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeee eeee, eeeeeee, eee α,β-eeeeeeeeeee eeeeeee.[‌888‌] Meeeeeeeeeeeeeee (88eee%) eeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeee-8-eee eee eeeeeeeeeeee ee 88 eee 88% eeeee, eeeeeeeeeeee, eee eeeeeeeee eeeeeee eee ee eeeeeeeee eeeeeeeeeeee.[‌88‌,‌88‌] M eeeeeeeee eeeeeee ee eeee eeeeeeee eee eeee eeee eeeeeeee, eee eeee eeee eeeee eeeeee (8888%).[‌88‌] Meeeee eeeeeeee-eeeeeeeee eeeeeee, eeee ee 8,8,8-eeeeeeeee-8-(8,8,8-eeeeeeeeeeeeeee)eeeeeeee, eee ee eeeeeeeee eeee eeeee eeeeeeeeeee eeeeeeeeeeeeee eeeeee ee eeeeeeeeeeeeee eeeeeee eeeeeee eee eeee eee e eeeeeeee.[‌888‌]

Meeeee 88 M-Meeee-Meeee Meeeeee eee eee Meeeeeee-Meeeeeeee Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee Meeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee ee α,β-eeeeeeeeeee eeeeee eee eeee eeeeee eee 8,8- ee eee 8,8-eeeeeeee eeeeeee. Me eee eeee eeeee eeee eeeeee eee Meeeeee eeeeeeee ee eeeeeeee ee eeeeee eeeeeeeee, eeeee eeeee eeee ee eeeeeeeee eeeee ee eeeeeee eeeee eeeeeeee eee 8,8-eeeeeeee.[‌888‌] Meeeeeeeeeee, eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee β-eeeeee-α,β-eeeeeeeeeee eeeeeee eee eeeeeee. Me eee eeeee eeee ee eeee eeeeeeeeeee, ee eee eeeeeee ee eeeeeee, eee 8,8-eeeeee eee eeeeee eeee e 88-eeee eeeeee; eeeeeee eee eeeeeeee eeeeeeeeeee eeeeeee eeeeeeeee ee eee 8,8-eeeeeeee eeeeeee. Mee eeeeeeee ee eeee eeeeeeeeeee eee ee eeeeeeeee ee eeeeeeee eeeee eeee ee eeeeeeeeeeeee eee 8-(eeeeeeeeeeeee)eeeeeeee ee eeee eeeeeeeeeee eee 8,8-eeeeee eeee eeeeeeee eeeee ee eeeeeee eeee eeee 88 eeeeeee.[‌888‌,‌888‌] Meee eeeeeeee, eee eee ee eeeeee ee e eeeeeeee eee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeee eee eeee eeeeeeee. M eeeeeee ee eeee eeeeeeeeeee ee eeee eeee 8,8-eeeeeeee ee eeeeeeee eeee α,β-eeeeeeeeeee eeeeeee.[‌888‌]

M eeeeee ee eeeee eeeeeeee eeee eeee eeee ee eeee eeeeeeeeeeee ee eeeee eeeeeeeeeee eeee eeeeeee. Meeeeeeeeeeeeee eeeeeee eee ee eeee ee eeee eeee eeeeeeeeeeee, ee eeeeeeeeeee ee eee eeeeeeeee ee 8-eeeeeee-8-eeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeeee eeee 8-eeeeeee-8,8-eeeeeeeeeeeeeeeee-8(8M)-eee.[‌888‌] Meeeeeeeeeeeeee eeeeeee ee eeee eee eeeeeee ee eeeeee eee eee eeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeee ee β-eee eeeeeeeeee, eeeeeee ee eee ee-eeeeeeeeeeee ee eee eeeeeeeeeee eeeeeee eeee eeeeeee eeee 88% ee.[‌888‌‌888‌] Meeeeeeee(MMM) eeeeeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeeeee eeeeeee eeee eeeeeee eeeeeeeeeee ee eeeee eeeeeee. Meee eeeeeeeeeeeee eeeeeeeeeee, eeeeee ee 8888% eee ee eeeeeeee ee 88 eeeeeee ee eeee eeeeeeeeeee, eeeee eeee 8eee% ee eee eeeeeeee. Mee eeeeeeeeeeee, eeeeeee, eee eeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeee eee eeee e 8% eeeee ee eeeeeeee.[‌88‌] Meeeeee eeeeeeeee eee eeee eeeeeeee eeeee eee eeeeeeee eeeeeee ee eeeeeee eeeeee 8 (eee Meeeee 8). Me eeee eeee, 8eee% ee eee eeeeeeee eeeeeeee eeee eeeeee 8 eee eeeeeeee(MM) eeeeeeeeeeee eeeeeeeee eeeeeeeeeeeee eeee eee eeeeeeeeeee ee >88% eeeee ee 8eeeee ee eeee eeeeeeeeeee.[‌88‌] M eeeeeee ee eeeeeeeee eeeeeee eee eeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeee(MM) eeeeeee eee eeee eeee ee eeeeeee eeeeeeeeeeee eee eeeeeeeeeeeee eeee eeeee eeeeeeeeeee eeeeeeeeeeeeee eeeeee.[‌88‌] Meeeeeeee MMM eeeee eee ee eeeeeeeeeee eeee eeeeee eeeeee ee eeeeeeeee eeeeeee, eee ee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeeee eeee eeee eeeeeee eeeeee, eeeee eeee, eee eeeeeeeee eeeeeee eeee eeeee eeeeeeeeeee eeeeeeeeeeeeee eeeeee.[‌88‌] Mee eeeeeeeeeee ee eeeeeee eeeeeee eee eeeeeee eeeeeeeeeeeeeeee[‌88‌,‌888‌] [(MeM)8M(M)MM] ee eeeeeee eeeeeeeeeeeeeee[‌88‌] [(MeM)8M(M)Me] eee eeee eeee ee eeeeeee eeeeeee (eeeeeeeee α,β-eeeeeeeeeee eeeeeee) eeee eeeeeeeeeee eeeeeee eeeeeeeeee. Mee eeee eeeeeeee eee ee eeeeeeee eeeee eeeeeee eeeeeeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeee eeeeeeeeeeeeeeee.[‌888‌] Meeeeeeee ee eeeeeeeee eee eeeee eeee eeeeeee eeee eeeeee eeeeeeeeeeee eeeeeee ee eeeeeeeeeee eeeeeeeeee.[‌888‌,‌888‌]

Me e eeeeee eeeeeeee e eeeeeeee eeeeeee eeeeeee eeeee, eeee eeeeeeee ee eeeeeee ee eee eeeeeeee eee eeeee eeee eeeeeeeeeee eeeeeeeeeee ee eee eeeeeeee eeeeee eeeeeee ee eeeeee eeeeeeee 88, ee eeeee ee Meeeee 88. Me eee eeeeeee eeeee (eeeeeeee ee eeeeeee) ee eeeeeeee ee eee eeeeee eeeeeeee ee eee eeeeeeee, eeee eeee eeeeeeeee eee ee eeee ee eeeeeeeeee eeeeeeeeeeeee,[‌888‌‌888‌] eeeeee β-eeeee eeeeeee eeee eeee ee eeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeee ee Meeeeee ee Meeeeee eeee Meeeeeeeeee Meeeeeeeeee[‌888‌‌888‌]

Meeeeeeeeee, (M)-eee-8-eee-8,8-eeeeee (eeeeeeee ee eeeeeeeee ee eeeeee eeee eeeeeee eeeeee) eeeee eeee eeeeeeeeeeeeee eeeeeee ee eeee 8-eeeeeee-8,8-eeeeeeeeeeee-8-eeeeeeeeeeeee.[‌888‌] Meeeeee eeeeeeeee ee eeee eeeeeeeeeee eeeeeee ee eeeee ee Meeeee 88; eeeeeeeee ee β-eeeeeee 88 eeee eeeeeeeeeeeeee eeeeeee eee eeeeee eeeeeeee(MM) eeeeeeee ee eeeee eeeeeeeeeee eeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeeeee 88, eeeeeeeeeeeee ee eee eeeeeeeeeeee eeeee. Me eee eee Meeee eeeee, eeeeeeee(MM) eeeeeeee eeeee eee eeeeee eeeeeeee eeeee (88%) eee eee eeeeee eeeeeeeeeeeeee eeeee (88:88).[‌888‌]

Meeeee 88 Meeeeeeee ee e Meeeeeeeeeeeeee ee Meeeeee-Meeeeee Meeeeeeeeee eeee e β-Meeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeeeee 88 ee eeeeeeeeeee 88 eeeee ee eeeeeeeeeee eeeee eeeeee 88 ee α-eee eeeeee, ee eeeee ee Meeeee 88. Mee eeeeeeee ee eeeeeeeee ee e eeeeeeeeeee ee eeeeeeeee eeeeeee eee 88-eeeee-8 eee eeeeeeee eeeeeee e 8,8-Meeee eeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeee Meeee Meeeee ee α-Mee Meeeee eeee Meeeeeeeeee eee Meeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 MeM88 M8 Meeee (%) Mee
(MM8)8Me MMM Me 88 [‌888‌]
eMe MMM Me 88 [‌888‌]
e-Me MMM Me 88 [‌888‌]
Me MMM Me 88 [‌888‌]
8-MeM8M8 MMM Me 88 [‌888‌]
8-MeMM8M8 MMM Me 88 [‌888‌]
Me MMMMM Me 88 [‌888‌]
Me MMMMM e-Me 88 [‌888‌]
Me MMMMM Me 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeee(eeeeeeeeeeeeeee)eeeeeeeeeeee; Meeeeee Meeeeeeee eee eee Meee(MM) Meeeee Meeeeeeee Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee e Meeeee:[‌888‌]

Meeeeeeee eeee (Meeeeee; Meeeee, Meeeeee Meeeeeeee, Meeeeeeeee Meeeee MMM), Meeeeeeee (8888), e88, eeee eeeeeeeeee eeee Meee Meeee&Meee, Mee.

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me eeeeeeeeeeee (88.8e, 8.88eee) ee e eeeee eeeeee eeee e eeeeee eeeeeeeee eee e eeeeee eeee eeee eeeee MMMMM (88.8e, 8.88eee), eeeee MeM8 (888ee, 8.8eeee), eee MM8Me8 (88eM). Mee eeee eee eeeeee ee 88°M eee 8e, eeee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeeee eee eeeeeee (8888e), eeeee eee eeeeeeeeeeee eeee eee eeeeeeeeee eee ee eeeee ee eeeeeee eeeeeeee ee eeeeeeeeeeee (ee 888°M/8.8Meee).

Meeeeeeeeee Meeeeeeeeeeeee Meeeee; Meeeeee Meeeeeeee eee eee Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee Meeeeee Meeee Meeeeeee 88:[‌88‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me e eeee ee e eeeeee (8eeee) eee MMMMM (8.8eeee) ee MM8Me8 (8eM) ee 88°M eeeee e M8 eeeeeeeeee eee eeeee eee eeeeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeeee eeeeeeee (88, 8eee%). Mee eeeeeee eee eeeeeee ee 88°M eee 8e, eee eeee eee eeeeeeee eee eeeeeeee ee eee eeeeeeee ee eeeeeeee (8.8eM); eee eeeeeee eee eeeeeee ee eeee ee ee eee M8M eee eeeee. Meeee eeeeeee eeeeee (eeeeeee eee eeeee) eee eeeeee eee eeeeeeeeeeeeee eeee eee eeeeeeeeeee eeeeeeeeeeeeee eeeee; eeeee: 8888%.

8-Meeeeee-8-eeeeee-8-(eeeeeeeeeeeeeee)eeeeeeeeeeeeee; Meeeeee Meeeeeeee eee eee Meeeee(MMM) Meeeeee Meeeeeeee Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee e Meeeeeeeeeeeee Meeeee:[‌888‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me e eeeee-eeeee eeeee eeee eeeee eee MM8Me8 (8eM), eeeee MeMe8 (88ee, 8.88eeee), eee 8-eeeeeee-8-eeeeeeeeeeeeee (888μM, 8eeee). Mee eeee eee eeeeeee eee 88eee, eeee MMMMM (888μM, 8.8eeee) eee eeeee. Mee eeeeeee eee eeeeeee eee 88eee, eee eeee eee eeeeeeee eee eeeeeeee eeee eee. MeMMM8 eeee (8eM). Mee eeeeeee eee eeeeeeeee eeee Me8M (8×8eM), eee eee eeeeeeee eeeeeeee eeee eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeeeee/Me8M 88:8) ee eeee e eeee eeeeee eee; eeeee: 88%.

Meeeeeeeeee Meeeeeeeeeeeee Meeeee; Meeeeee Meeeeeeee eee eee Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee Meeeeee Meeee Meeeeeeee-Meeeeeeee Meeeeeeee(MM) Meeeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me e eeeeeee eeeeeee ee e eeeeee (8eeee) eee eeeeeeeee-eeeeeeeee eeeeeeeee(MM) eeeeeeee eeeeeeeee [Me(MMM8)8] (888ee) ee eeeeeeeee MM8Me8 (8eM) eee eeeee MMMMM (8eeee). Meeee 8.888e, eee eeeeeee eee eeeeeeee eee eee eeeee eee eeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeeee eeee eee. Me8MM8 eeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MM8Me8) ee eeee eee eeeeeeeeeee eeeeeeeeeeeeee eeeee; eeeee: 8888%.

Meeeeeeeeee Meeeeeeeeeeeee Meeeee; Meeeeee Meeeeeeee eee eee Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee Meeeeee Meeee eee Meeeeeee Meeeeee ee Meeeee 88:[‌888‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me e eeee ee eeeeee 88 (88.8ee, 8.888eeee) ee MM8Me8 (8eM) eee eeeee 8M Me(MeMe)8 ee eeeeeee (88μM, 8.888eeee) eee eee eeeeeee eee eeeeeee eee 8e. Mee eeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeee eeeee eeeeeee eeeeeeee eee 88eee. Mee eeeeeee eee eeee eeeeeeeee ee MM8Me8 (8.8eM), eeeeee ee 8°M, eee eee eeeeee (8.88eeee) eee eeeee, eeeeeeee ee MMMMM (88μM, 8.88eeee). Mee eeeeeeee eee eeeeeee eee 88888e, eeee eeeeeeeeeeee eee eeeeeeeee ee eee eeeee eeeeee (eeeeeee eee eeeee), eeeeeeee ee eeeeee eee eeeeeeeeeeeeee, ee eeee eee eeeeeeeeeee eeeeeeeeeeeeee eeeee; eeeee: 8888%.

Meeeeeeeeee Meeeeeeeeeeeee Meeeee; Meeeeee Meeeeeeee eee eee Meeeeee Meeee Meeeeeeee 8,8-Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee α,β-Meeeeeeeeee Meeeeee:[‌888‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me e eeeeeeeeee ee MeM (8.8e) ee eeeeeee (8eM) ee 88°M eee eeeee e eeeeeee ee ee α,β-eeeeeeeeeee eeeeee (8eeee) eee MMMMM (8.8eeee) ee eeeeeee (8eM). Mee eeeeeee eee eeeeeee eee 8.88e, eeeeeeee eeeeeee Meeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeeeeeee eeeeeeeeeeeeee eeeee; eeeee: 8888%.

Meeeeeeeeee Meeeeeeeeeeeee Meeeee; Meeeeee Meeeeeeee eee eee Meeeee-Meeeeeeee Meeeeeee ee Meeeeeeeeeeeee Meeeeee ee Meeeeee:[‌888‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me e eeeeeee eeee ee eee eeeeee (8eeee) eee M8 (8eee%) ee MM8Me8 (88eM) ee 8°M, MMMMM (8.8eeee) eee eeeee eeeeeeee. Mee eeeeeeee eee eeee eeeeeee ee ee eee 8888eee, eeeee eeeee eeee M8M (88eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee 88% ee Me8M8M8, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee eee eeeeeeeeeee eeeeeeeeeeeeee eeeee; eeeee: 8888%.

8-Meeeeee-8-eeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeeee; Meeeeee Meeeeeeee eeee Meeeeeeeeeeeeee Meeeeee:[‌888‌]

Meeeeeeee eeee (Meeeee; Meeeeeee; Meeeeeee, Meeeeee Meeeeeeee, Meeeeeeeee Meeeee MM), Meeeeeeee (8888), e888, eeee eeeeeeeeee eeee Meee Meeee&Meee, Mee.

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

8-Meeeeee-8,8-eeeeeeeeeeeeeeeee-8(8M)-eee (8.88e, 8.8888eee) eee eeeeeeeee ee eeeee eeeeeee (88eM) ee e eee-eeeeee eeeee eee eeeeee ee 88°M eeeee e M8 eeeeeeeeee, eeee e eeeeeeeee (8°M) eeee ee 88% Me8MeMM ee eeeeeee (88eM, 8.88eee) (MMMMMMM: eeeeeeeeee) eee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeee ee 88°M eee 88eee. Mee eeeeeeee eee eeee eeeeeeeeeee eee e eeeeeee eeee e eeeeeee ee MeMM (888eM) eee eeeee MMe (888eM) ee 88°M eeeeee eeeeeeeeeee e eeeeeeeeee eeeee eeeeeeeeee. Mee eeeeeee eee eeeeeee eee 8e, eeee eeeeee eeee e eeeeeee ee eeeee MMe (888eM) eee eee eeeee (8888eM), eeeeeeeee eeee MM8Me8 (8×888eM), eee eee eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee e eeeee eeeeeeeeee MeMM (88ee) ee eeeee eee eeeee eeeeeee, eeeee eeeee ee eeee eeeeeee eeeeeee eeeeeeeeeeee.

Meeeeeeeeee Meeeeee Meeeeeeeee; Meeeeee Meeeeeeee eeee Meeeeee Meeeeeeeeeeeeee eee Meeeeee Meeeeee:[‌88‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me e eeee ee e eeeeee (8.8eeee) eee (MeM)8M(M)Me (8.88eM, 8.8eeee) ee eee MMM (8eM) eee eeeee e 8.8M eeee ee MeMM ee MMM (8.8eM, 8.88eeee), eee eee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 8888eee. Mee eeeeeeee eee eeeeeeee eeee M8M eee eeeeeeeee eeee eeeeee/MeMMe (8:8). Mee eeeeeee eeeee eee eeeeee eeee eeeee (8×), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeee eeeeeeeee ee eeeeeeeee ee eeeeee eee eeeeeeeeeeeeee ee eeee eee eeee eeeeeeeeeee eeeeeee eeeeeeeee; eeeee: 8888%.

Meeeeeeeeee Meeeeeeeee; Meeeeee Meeeeeeee eeee Meeeee Meeeeeeeeeee:[‌888‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

eMe8MM (88eeee) eee eeeeee eeeeeeeeeeee (88eeee) eeee eeeee ee e eeee ee e eeeeee (8eeee) ee MMM (88eM). Mee eeeeeee eee eeeeeee ee ee eee 888e, eee eeee eee eeeeeeee eee eeeeeeee eeee M8M, eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeee eee eeeeee eeee 88% MMe, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eee eeeeeeeeeeeeee ee eeee eee eeeeeeeeeee eeeeeeeee; eeeee: 8888%.

Meeeeeeeeeeee; Meeeeee Meeeeeeee eee eee Meeeeeee ee Meeeeee ee Meeeeee eeee Meeeeeeeeee:[‌888‌]

MMMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

M eeee ee ee α-eeee (ee α-eeeeeeeeeeeeeeeee) eeeeee (8.8eeee) ee MMM (8eM) eee eeeee eeeeeeee ee e eeeeeeeeee ee MMM (8.8eeee) ee MMM (88.8eM) ee ee. Mee eeeeeee eee eeeeeee eee 888e, eeee eeeeee eeee M8M, eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeeee eeeeeeee eeee eeeeee eeee 8% MMe, MeMMM8 eeee, eee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/Me8M 8:8) ee eeee eee eeeeeeeeeeee; eeeee: 8888%.

References