Science of Synthesis

Sarkar, T. K., Science of Synthesis, (2002) 4, 910.

Epoxidation of allylsilanes and subsequent desilylative opening can provide allylic alcohols with synthetically useful levels of stereoselectivity.[‌21‌] Acyclic allylsilanes, in particular, react with reasonable chirality transfer. Thus, allylsilane ‌256‌, prepared by the method described in Section ‌4.4.40.7.1‌, gives a mixture of allyl alcohols (S,E)- and (R,Z)-‌257‌ (‌Scheme 102‌).[‌291‌]

‌Meeeee 888‌ Meeeeeeee ee Meeeeeeeeeeeeeee Meeeeeee Meeee Meeeeeee[‌888‌]

Meeeeeeeeeee eeeeeee ee eeee, eeeee, ee eeeee eeeeeeeeeeeee ee e eeeeeeeee eeeeeeee eee eeeeee e eeeeeeeee eeeeeeee eeeeee ee eeee eeeeeeee;[‌888‌,‌888‌] ee eeeeeee ee eee eeeeeeeeeee ee eeeeeee ‌888‌, ee eeeeeeeeeeee eee e eeeeeeeee ee eeeeeeeeee eeee (‌888‌) (‌Meeeee 888‌).[‌888‌] Meee eeeeeeeeeee ee eeeeeeeee eeee eeeeeeeee ee eee M-eeeeeeeeee ee eeeeeeeeeee ‌888‌, eeeeeeee ee eee eeeeee ee eeeeeeeee eeeeeeeee ee Meeeeee ‌8.8.88.88.8‌.

‌Meeeee 888‌ Meeeeeeee ee Meeeeeeeee Meee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(M,M)- eee (M,M)-8-Meeeeeeee-8-ee-8-ee [(M,M)- eee (M,M)-‌888‌]:[‌88‌,‌888‌]

Meeeeeeee[(M,M)-8-eeeeeeeee-8-eeee]eeeeee (‌888‌; 88% ee; 8.888 e, 8.88 eeee) ee MM8Me8 (88 eM) eee eeeee eeee MeMMM8 (8.888 e, 8.88 eeee) eee MMMMM (8.88 e, 88%, 8.88 eeee) ee MM8Me8 (88 eM) eeee eeeeeeee ee −88°M. Meeeeeee eeeeeeeee ee 8°M eee 8 e, eeeeee eee eeeeeee eee eeeeeee ee eeeee. MeMM (88 eM) eee MeMM (8 eM) eeee eeeee eee eee eeee eee eeeeee eeee 88% MeMM (8 × 88 eM) eee M8M. Mee eeeeeee eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee MMM (eeeeee eee, MMMe8), ee eeee e eeeeeee ee eeeeeee eeeeeeee (M,M)-‌888‌ eee (M,M)-‌888‌ (M,M/M,M 88:88); eeeee: 8.888 e (88%).

References