Epoxysilane rearrangement induced by a carbanion generated by conjugate addition of enolates of chloroacetate and alpha-chloroacetamides: formation of functionalized cyclopropane derivatives.
[reaction: see text] Reaction of an enoate bearing an epoxysilane moiety at the alpha-position with lithium enolate of 2-chloroacetamide afforded highly functionalized cyclopropane derivatives via a tandem process that involves Michael addition, ring opening of the epoxide, Brook rearrangement, and intramolecular alkylation.
Okamoto
Noriko
N
Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8553, Japan.
Sasaki
Michiko
M
Kawahata
Masatoshi
M
Yamaguchi
Kentaro
K
Takeda
Kei
K