Science of Synthesis

Singer, R. D., Science of Synthesis, (2002) 4, 242.

Selected applications of silyllithium reagents are outlined here. The examples presented are intended to give a general sense of how these reagents may be used in synthesis.

Meeeeeeeeeeeeeeeeeeee eeeeeeee eee eeee eeeeeeeeeeee[‌8‌] eee eeeeee ee e eeeeeee eeeeeee ee Meeeeeee eeeeeeee. Meee eee eeeee eeeeeee eeee eeeeeeee eeeeeeeee ee eeee α-eeeeeee-eeeeeeeeeee eeeeeee, eeee ee ‌8‌ eee ‌8‌;[‌88‌,‌88‌] eeeeeeeee, β-eeeee-eeeeeeeeeee eeeeeee eeee eeee eeeeee ee eeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeeeeee ee eeee eeeeeee (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Meeeeeee ee Meeeeeeeeeeeeeeeeeeee Meeeeeee eeee Meeeeee eee Meeeeeee Me Meee α-Meeeeee-Meeeeeeeeee Meeeeee eee Meeeeee, Meeeeeeeeeee[‌88‌,‌88‌,‌88‌]

Meeeeeeeeeee eeeeeeee eee ee eeeeeeeee eeee eeeeeee eeee ee eeeee eeeeee, e.e. eeeeeeeeeee, ee eeee e eeeeeeeeeeeeeeee, ee eeee e eeeeeeeeeeeeeeeeeee, eeee ee eeeeeeeeeeeeeeeeeeeee, ee eeee e eee Me—Me eeee. Meee eeeeeeeee eeeee eeeeee eeee eeeeeeeeeeee eeeeeee, ee eeee ee eeee Meeeeeee eeeeeeee, ee eeee eeeeeeeeeee, eeee ee ‌8‌, eee eeee eeeeeeee eee ee eeeeeeee eeeeeeee ee eeeeeee eeeeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeee eeee e eeeeeeeeeee eeeeeee (eee eeee Meeeeee ‌8.8.88‌). Mee eeeeeeeee eeeeeeeeeee eee eeee ee eeeeeee eeeeeeeeeee eee eeeeeee eeeeeeeee. Meee eeeeeeeee ee, eeeeeee, eeeee eeee eeee eeee 8 eeeeeeeeeee ee e eeeeeeeeeeee eeeeeee, eeee ee ‌8‌, ee eeee eeeeeee eeeeeeee, e.e. ‌88‌[‌88‌,‌88‌] (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Meeeeeee ee Meeeeeeeeeeeeeeeeeeee Meeeeeee eeee Meee Meeeeeeee Me Meee Meeeeeeeeee eee Meeeeee Meeeeeee[‌88‌,‌88‌,‌88‌]

Meeeeeeeeeeeeeeeeeeee eeeeeeee eeeeee ee eeeeeeeeeeee Me—Me eeee eeeeeeee (Meeeeee ‌8.8.88.8.8‌) eeee eeee eeeee ee eeeeeee eeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeeeeee α,β-eeeeeeeeeee eeeeeee,[‌88‌,‌88‌] ee eeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeeee (‌8‌) eeee eeeeeeee-8-eeeee (‌Meeeee 8‌). Meee eeeeeeeeeee eeee eeeeeeeeeee eeeeeeeee (eee Meeeeee ‌8.8.88‌), eeeee eeeeeee eeeeeee eeeeeee eeeeeeeee eeeeeeee eeee e eeeeeee ee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee, eeee eeeeeeee eee eeeeeeeeee ee eee 8-eeeeeeee (‌Meeeee 8‌). Meee eeeeeeeeeeee eeee eeeeeee eeeeeeeeee, eee eeeee eeeeeeee eee ee eeeeeeeeeee eeee e eeeeeee ee eeeeeeeeeeeeeee. Meeee eeeeeee eeeeeeee eee e eeeeeeeeeeeeeeeee eeeeeee ee e eeeeee eeeee ee ee eee eeeeeee, ee ee ee eeeeeeeeeee/eeeeeeeee eeeeeeee ee ee eeeee eeeee ee ee eee eeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeee Meeeeeee ee Meeeeeeeeeeeeeeeeeeee Meeeeeee eeee α,β-Meeeeeeeeee Meeeeee[‌88‌,‌88‌]

Meeeeeeeeeeeeeeeeeeeeeeeee (‌8‌) eee eeee eeeee ee ee e eeeeeeee eeeeeee eee eeeeeeeeee eeeee eeee eeeeee eeee eeeeeee eeeeeeee, e.e. ‌88‌, ee eeeee eeeeeeee eeeee eee ee eee eeeeeeeeeee (‌Meeeee 88‌).[‌8‌] Meee eeeeeeee ee eeeeee eeee eee eeeeeeee ee eeeee eeee eeeeee ee eeeeeeeeeeeee eee eee eeeeeeeee ee eeeeeee eeeeeeee. Meeeee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeeeee (‌8‌) eeee eeee eeeeeeeee (eee ‌Meeeee 8‌), eeeeeeee eeee M,M-eeeeeeeeeeeeee[‌88‌,‌88‌] ee eeeeee eeeeee[‌88‌] eeeee ee eeeeeeeeee eeeeeee ‌88‌. Me eee eeeeeeee ee M,M-eeeeeeeeeeeeee eeee eeeeeeeeeeee ‌8‌ ee eeeeeeee ee −88 eeeeee eeee −88°M eeee eeeeeeeeeee ‌88‌ eeeeee.[‌88‌] Mee eeeeeeeeeee ‌88‌ eee ee eeeeeee eeeeeee eeee eeeeee ‌8‌ ee eeeeee eeeeeee eeeeeeee ‌88‌, eeeee eee ee eeeeeeeeeeee eeeeeeeeeee eeeeeeee ee eeeeeeeee eeeee eeeeeeeeeee eeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeeeeeeeeeeeeeeee eeee Meeee Meee Meeeee, Meeeee Meeeee, M,M-Meeeeeeeeeeeee, eee Meeeeeeeeee[‌8‌,‌88‌,‌88‌,‌88‌]

α-(Meeeeeeeeeeeeee)-eeeeeeeeeee eeeeeeeee eee eeeeeee eee ee eeeeeee eeee eeeeeeeeeeeeeeeeeeeee (‌8‌) ee eeeeeeeeeeeeeeeeeeee eeeeeeee (‌Meeeee 88‌),[‌88‌] ee eeee eee eeee eeeeee eeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee (‌8‌)[‌88‌] ee eeee eee eeeeeeeeeeeee eeeeeeeee ee eeeeeee.

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeeeeeeeeeee eeee e α-(Meeeeeeeeeeeeee)-Meeeeeeeeee Meeeeeee[‌88‌]

Mee M-eeeee eeeee ee eee eeeeeeee eeeeee eee eeeeeee ‌88‌ eee ee eeeeeee ee eeeeeeeee eeee eeeeeeeeeeee ‌8‌ ee eeee eee eeeeeeeeeeeee eeeeeeeee eeeeee. Meeeeee, 8-eeeeeeeeeeeeeee ‌88‌ eeeee eeee ‌8‌ ee eeee eee eeee-eeeeee, eeeeeeeeeee M-(eeeeeeeeee)eeeeeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeeeeeeeeeeeeeeee eeee M-Meeee-Meeeeeeeeee Meeeeeee Meeeee, Meeeeee, eee Meeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

MM8M8	Meeee (%)	Mee
MMeMe	88	[‌88‌]
MMe8	88	[‌88‌]
	88	[‌88‌]
eeeee-8-ee	88	[‌88‌]
	88	[‌88‌]

‌Meeeeeeeeee 88‌

e eeee-‌88‌ eeee eeee-‌88‌.

e eee-‌88‌ eeee eee-‌88‌.

Meeee e eeeeeee ee eeeeeeeeeeee eeeeeeee eeee eeeeeee ee eeeeeeeee, ee eeeeeee ee eeeeee eeeeeeeeeeeeeeeeeeeeeeeeee (‌8‌) ee eee eeee eeeeeeeee eeeee ee eee eeee ee eeeeeeeeeee eee eeee eeeee ee eeee.

References