Science of Synthesis

Ager, D. J., Science of Synthesis, (2010) 47, 101.

In the presence of a Lewis acid, α,β-epoxysilanes, which are readily available by epoxidation of the corresponding vinylsilanes, undergo nucleophilic attack at the carbon atom bearing the silyl group to provide a β-silyl alcohol which may then undergo elimination to give an alkene.[‌7‌,‌74‌] One example of this procedure involves the addition of an organocuprate with regio- and stereochemical control (‌Scheme 24‌).[‌23‌]

‌Meeeee 88‌ Meeeeeee ee ee Meeeeeeeeeeee eeee ee α,β-Meeeeeeeeee[‌88‌]

M eeeeeeeeeeeee ee eee eeeeeeeeeee ee ee α-eeeee eeeeeeee ee eeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee eee e Meeeeeee eeeeeee. Meeeeeeeee eeeeeeee ee eee Meeeeeee eeeeeee ee eee eeeeee eeeeeeee eeeee eeeee e β-eeeee eeeeeee ‌88‌. Meee eeeeeee eee eeeeeee eeeeeeeeeee ee eeee ee eeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeee ee e Meeeeeee Meeeeee eeee ee α,β-Meeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

eeeeeee-8-(Meeeeeeeeeeeee)eeeee-8-ee (‌88‌):[‌88‌]

Me ee eee-eeeeee eeeeeee ee MeMe8 ee Me8M [eeeeeeee eeee 8,8-eeeeeeeeeeeee (8.88 e, 8.88 eeee) ee Me8M (8 eM) eee Me (888 ee, 8.88 eeee) ee Me8M (88 eM)], eeee eeeee 8.88 M MeMeMe ee Me8M (8.8 eM, 88 eeee) eee 8-eeeee-8-(eeeeeeeeeeeeee)eeeeeee (888 ee, 8.88 eeee). Mee eeeeeeeee eeeeeee eee eeeeeee eee 88 eee eeeee eeeeeee ee ee, eee eeee eeeee ee eeee eeeeeeeeeee eee ee eeeeeeeeee 8 e. Mee. MM8Me (88 eM) eee eeeee, eee eeeeeee eeeee eee eeeeeeeee eee eeeeee eeee eee. MeMMM8, eee eee eeeeeeee eeeeeee eeeeee eeee eeeeeeeee eeee Me8M (8 ×). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeeeeeee, eee eeeeeeeee ee eeeeeeeeeeeeee [Meeeeeee (88 e), Me8M/eeeeeee 8:88 ee 8:88] ee eeee e eeeeeeeee eeeeee; eeeee: 888 ee. Meee eeeeeeee eee eeeeeeeee ee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 888 ee (88%).

(M)-Mee-8-eee [(M)-‌88‌]:[‌88‌]

MM8•MMe8 (8.88 eM, 888 ee, 8.8 eeee) eee eeeee ee eee β-eeeee eeeeeee ‌88‌ (888 ee) ee MM8Me8 (88 eM). Mee eeeeeeeee eeee eee eeeeeee ee ee eee 8 e, eee. MeMMM8 eeee (88 eM) eee eeeee, eee eee eeeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 ×), eee eee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeeeeeee, eee eeeeeeeee ee ee ee eeee eee eeeeeee; eeeee: 888 ee (88%); (M/M) 88:8 (ee eeeeeeeeee ee eeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeee).

(M)-Mee-8-eee [(M)-‌88‌]:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeee eeeeeee ee eeeeeeee ee eee eee ee eeeeeee eeee eeeeeeee eee ee eeeeee eeeeeeeeeee ee eee eeeeeee.

Meeee eeeeeee ‌88‌ (888 ee, 8.88 eeee) eee eeeee ee e eeeeeeeeee ee eeeeeee-eeeeee MM (888 ee, 8.8 eeee, ee e 88% eeeeee ee eee) ee MMM (88 eM). Mee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 8 e, eee. MM8Me (8 eM) eeee eee eeeee, eee eee eeeeeee eee eeeeee eeee e eeeeeeee M8M/eeeeeee eeee. Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee M8M (8 ×), eeeee (MeMM8), eeeeeeeeeeee, eee eeeeeeeee ee 88°M ee eeee eee eeeeeee ee e eeeee eeeeee; eeeee: 888 ee (88%); (M/M) 8:88 (ee eeeeeeeeee ee eeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeee).

References