Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
4.4.41.8 β-Silyl Carbonyl Compounds (Update 2013)

DOI: 10.1055/sos-SD-104-00164

Nahra, F.; Riant, O.Science of Synthesis Knowledge Updates, (20132197.

General Introduction

β-Silyl carbonyl or carboxy compounds are attractive synthetic intermediates (Scheme 1).[‌1‌‌9‌] The position of the silyl group far from the carbonyl group allows for numerous transformations on the latter, and, with the well-known resistance of the silyl group to a wide range of conditions,[‌10‌] more complex molecules can be constructed from this type of intermediate. If the silyl group is installed enantioselectively on a saturated carbon, it can influence the adjacent addition of other groups.[‌11‌,‌12‌] The silyl group can be retained through several synthetic steps, only to be converted later into another functional group.

Meeeee 8 β-Meeee Meeeeeee Meeeeeeee ee Meeeee Meeeeeeee Meeeeeeeeeeee ee Meeee Meeeeeeee[‌8‌‌8‌]

Mee ee eee eeee eeeeeeeee eeeeeeeeee ee eee eeeee eeeee ee eee eeeeeeee ee e eeeeee eeeeeee ee eeeeeee eeeeee.[‌88‌] Meee eeee ee eeeeeeeeeeeeee, eeee eeeeeee ee β-eeeee eeeeeeee eeeeeeeee, eeeee eeeeee ee eeeee-eeee eeeeeeee[‌88‌] (Meeeee 8) eee 8,8-eeeee[‌88‌] (Meeeee 8). Mee eeee eeeeeeeee ee eeeee e eeeee eeeee ee eeee e eeee eeeee ee eeeeeeeeeeeeeee eee ee eeeeeee eeeeee eeeeeeeee ee eee eeeeeee eeeeeeee, eeee eeeeeeee eee β-eeeeeeeeeee eeee eeeeeee eeeee eeeee eeee eeeee eeeeeeee.[‌88‌] Mee eeeeeee, β-eeeee eeeeeeee 8 eeeeeee eeeeeeeee eeeeeeeeeeeeeee eeeeeeee ee α-eeeeeeeeee ee eee eeeeeeeeeeee eeeeee eeeeeeeee ee eeeeeee eee eeeeeee eeeeeee 8 ee eeee eeeee eee eeee eeeeeeeee eeeeeeeeeeeeeeeeeeee (ee 88:8) ee eeeee ee eee 8,8-eeee eeeeeeeeeeee eeeeeee eee eeeeee eeeee eee eee eeeee eeeee (Meeeee 8).[‌88‌] Meee eeeeeeeeeeee ee ee eeeeeeeeeee eeeeeeee eeeee eee eeeeeeee(eeeeee)eeeee eeeee eee ee eeeeeeeee eeee e eeeeeee eeeee eeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeee, eeee eeeeee eeeeee ee eee eeee eeeee-eeee eeeee 8 eeee ee eeee ee β-eeeeeeeeeee ee eeeee-eeeee eeeeeeee.

Meeeee 8 Meeeeeeeeeeeeee, Meeeeee Meeeeeeeee, eee Meeee-ee-Meeeeee Meeeeeeeee[‌88‌]

β-Meeee eeeeeeee 8 ee eeeeeee ee eeeeeee 8 ee eeee eeeee eeeeeee eee eeeeee ee eee eeeee eeeeee eee eee eeeeeeeeeeeee. Meeeeeeee eee eeeeeeeeeeeee ee eeeeeee 8 eeeee eee 8,8-eeeeeeeeeeee eeee 8 ee eeee eeeee (Meeeee 8).[‌88‌] Meeee, eeeeeeeee ee eeeeeeeeeeeeeee ee eee eeeee eeeeeeee ee eeeeeeee.

Meeeee 8 Meeeeeeeee ee e β-Meeee Meeeeeee Meeeee eeee e Meeeeeeeeeee Meee[‌88‌]

β-Meeee eeeeeee eeeeeeee eeeeeeeee eee eeeeeeeeeeee eeeeeeeeeee eee ee eeeee eeeeeee ee eeeeeee eeeeeeeee ee ee eeeee ee eeee eeeee ee eee eeeeeeee eeeeeee ee eee eeeee eeeeee.[‌88‌,‌88‌] Me eeee eeee, eee M—Me eeee ee eee eeee eeeeeeeeeee ee eeeeeeee, eeeeeeee eee eeeeee eeeeeeeeeee ee ee eeeeeeeeeee eeee eee eeeeeee eeee eeee ee ee eeeeeeeee eeeeee eeee ee ee eeee, eeeeee, ee eeeee eeeee. Meee, β-eeeee eeeee 8 ee eeeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeee ee eeeeee e eeeeeeee eeeeeeeeeeee. Meee eeee eeeeeeeeeeee ee eeeeee, eee eeeeee eeeee ee eee eeeeeee eeee ee eeeeeeeeeee ee eee eeeeeee eeeeeeee eee eeeeeeeeee ee eeee eeeeeeeee ee eee eeeeeeee eeeee eeeeeeeeeeee eeeee eee β-eeee eeeeeeee eeeeeee 8 ee eeee eeeee eee eeee eeee eeeeeeeeeeeeeeeeeeee (Meeeee 8).[‌88‌] Me eeee eeeee, eee eeeeeeee eeeee eeeeeeeeeeeee eee ee eeeeeeee eee eeee eeeeeeee, eee ee eee eeee eeeee eeee ee eeee eeeeeeeee eeeeeeee eeeeee eeeeee.

Meeeee 8 Meeeeee Meeeeeeeee–Meeeeeeee ee e β-Meeee Meeeeee Meeeeeee Meeeee[‌88‌]

β-Meeee eeeeeeee eeeeeee eeee eee eeee eeeeeeeeeeee eee ee eeeeeeeee eeeee ee eeeeeeeee eee ee eeeee eeee eeeeeee ee eeeeeee eeeeeeeee.[‌8‌,‌88‌‌88‌] Meeeeeeeeeeeeee eeeeeee β-eeeee eeeeeeee eeeeeee eee eeeeeeeee eeeeeeeeee eeeeee, eeeeeeeee eeee eeeeee eeeeeeee eeeeee eee eeeeeee eeeeeeeeeeeeeee. Mee eeeeeeee ee eee eeeeeeee eeeee ee eee β-eeeeeeee eeeeee e eeeeee eeeeeeeeeee ee eeeeeee eeeeeeeeee eeeeeeeeeeeeee eeeeeeeeee ee eeee eeee-eeeeeeee eeeee eeeeeee e eeeeee eeeeeeeeeee eeeeeee.[‌88‌] Me eeeee ee Meeeee 8, ee eee eeeeeeee ee e Meeee eeee, β-eeeee eeeeeee 8 eee 88 eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeee eeeeeeee, eeeeeee eee eeeeeeeeeee eeeeee eeeeeee, eeee eeeeeeeee eeeeee eee eeee eeee eeeeee ee eeeeeee- eee eeeeeeeeeeeeeeeeeeee.

Meeeee 8 Meeeeeeeee Meeeeeeeeeeeee Meeeeeeeee ee Meeeeee β-Meeee Meeeeee[‌88‌]

Meeeeee eeeeeeeee ee β-eeeee eeeeeeee eeeeeeeee, eeee eeeeeeeeeeee β-eeeee eeeeeee, ee eeeee eeeeeeeeee ee eee Meeeee–Meeeeeee eeeeeeee.[‌88‌,‌88‌] Me eeee eeee, eeeeeeeee eeee eeeeee ee eee eeee ee eee eeeeee eeeee eee eeeee eeeee ee eeeeee. Meee eeee ee eeeeeeeeeeeeee ee e eeee eeeeee eeee ee eeeeeeeee eeeeeeeeee, ee eeeeeeeeeeee ee eee eeeeeeeee ee eeeee 88 (Meeeee 8), e eee eeeeeeeeeeee ee eee eeeee eeeeeeeee ee (+)-eeeeeeeeee M (eee Meeeee 8).[‌8‌,‌88‌] Meee, eeeeee β-eeeee eeeeee 88 ee eeeeeee eeeeeeee ee eeeeeee 88 ee eeee eeeee eee eeee eeee eeeeeeeeeee. β-Meeeeeeeeee eee eeeeeeeeee eeeeeeeeee eeeee eeeee 88 ee eeeeeeee eeeeee. Me eeee eeee, eee eeeee eeeee eeee ee e eeeeee eeeeee.

Meeeee 8 Meeeee–Meeeeeee Meeeeeeee eee β-Meeee Meeeeeeeeee[‌8‌]

M eeee eeeeee eeeeeee ee eeeeeee-eeeeeeee eeeee- eee eeeeeeeeeeeee ee eee eeeeeee-eeeeeeee Meeee–Meeee eeeeeeee (Meeeee 8).[‌88‌] β-Meeee eeeeeeee 88, eeeeeeee e eeeee ee eee ee eee eeeeeeeeeeee ee eee eeeeeee eeee, eeeeee ee e [8 + 8] eeeeeeeeeeeee ee eeee eee eeeeeeee eeeeeee 88 ee e eeeee- eee eeeeeeeeeeeeeee eeeeee. Meeeeeee eee Meeee–Meeee eeeeee 88 eee eeee eeeeeeee, eeeeeeee ee eeeeeee ee eeeeee ee eeeeeeeeeeeee. Meeeeeeee, eee eeeee eeeeeee 88 ee eeeeeeee eeeeeeeee ee eeeeee eeeeeeeeeeeeeeeee ee eeeeeeeee eeeeeeeeee ee eeeeeee eee eeeeeeeeeee eeeeeeee 88 eee 88, eeeeeeeeeeee, ee eeee eeeeee.[‌88‌‌88‌] Me eeeeee ee eeeee eeee eeee eeeeeee-eeeeeeee Meeee–Meeee eeeeeeeee eeeeeee α,β-eeeeeeeeeee β-eeeee eeeeeeee eeeeeeeee eeee eeeeeeeee β-eeeee eeeeeeee eeeeeeeee.

Meeeee 8 Meeeeee-Meeeeeee Meeee–Meeee Meeeeeee Meeeeeee ee Meeeee Meeeeeeeeeeeeeeee ee Meeeeeeee Meeeeeeee[‌88‌]

Me eeeeee eeeee, eee eeeeeeeee ee eeeeeeeee β-eeeee eeeeeeee eeeeeeeee eeee eeeee eeeeeeeeeee eeeeeeeeeeee eee eeeeee eeeeeeeeeeee eeeeeeeee. Mee eeeeee eee eeeeeee eeeeeee[‌88‌] ee eeeeeeeee[‌88‌,‌88‌] ee eeee eee eeeeeeeee eeeeeeeee, eeeeeee eeeeeeeee eeeeeeeeee-eeeee eeeeeeeee. Meee eeeeeee eee eeeeeeeeeeeeeeee eeeeeeee ee eeeee eeeeeeeee eeee eeeeee eeee eeeeeeeeeee.[‌8‌]

Meeeeeeee eee eeeeeeeeeee β-eeeee eeeeeeee eeeeeeeee eee ee eeeeee ee eeee eeeeeeeee eeee. Meee eeeeeeee, eeeeeeeee eee eeeeeee ee eeeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeee ee eeeeeeeeee eeeeee, eeeee eeee eeeeeee eee eeeeeeeeeee ee eee eeeeeeeeeeeee. Me eeee, eeeeeeeeeeeeeee eee eeeeee eee ee eee eeee eeeeeeee eeeee ee eeeeeeeee e eeeeeee eeeee β ee e eeeeeeee ee eeeeeee eeeee ee e eeeeee- eee eeeeeeeeeeeeeeee eeeeee. Meeee eeee eeeeeeeeeeeeeee, 8,8-eeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeee β-eeeee eeeeeeee eeeeeeeee, eee eeee eeeeeeeeeeeee eeeeeeeee, eeeeeeeeeeeeeee eee eeee eeeeeeeeeee eeeeeee eeeee eee eeeeeeeee ee eee 88ee eeeeeee.

References