Epoxysilane rearrangement induced by a carbanion generated by conjugate addition of enolates of chloroacetate and alpha-chloroacetamides: formation of functionalized cyclopropane derivatives

Noriko Okamoto; Michiko Sasaki; Masatoshi Kawahata; Kentaro Yamaguchi; Kei Takeda

doi:10.1021/ol060469k

Epoxysilane rearrangement induced by a carbanion generated by conjugate addition of enolates of chloroacetate and alpha-chloroacetamides: formation of functionalized cyclopropane derivatives

Org Lett. 2006 Apr 27;8(9):1889-91. doi: 10.1021/ol060469k.

Authors

Noriko Okamoto¹, Michiko Sasaki, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda

Affiliation

¹ Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8553, Japan.

PMID: 16623577
DOI: 10.1021/ol060469k

Abstract

[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.