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Stereocontrolled construction of seven-membered carbocycles using a combination of Brook rearrangement-mediated [3 + 4] annulation and epoxysilane rearrangement.

作者信息

Nakai Yoshio, Kawahata Masatoshi, Yamaguchi Kentaro, Takeda Kei

机构信息

Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8551, Japan.

出版信息

J Org Chem. 2007 Feb 16;72(4):1379-87. doi: 10.1021/jo062282c. Epub 2007 Jan 23.

DOI:10.1021/jo062282c
PMID:17243723
Abstract

Reactions of delta-silyl-gamma,delta-epoxy-alpha,beta-unsaturated acylsilane with alkenyl methyl ketone enolate afford highly functionalized cycloheptenone derivatives via a tandem sequence featuring the combination of Brook rearrangement-mediated [3 + 4] annulation and epoxysilane rearrangement. The reactions using an opposite combination of three and four carbon units, in which an epoxysilane moiety was incorporated in the four-carbon unit, also give satisfactory results. Also, the possibility of chirality transfer from epoxide to remote positions via the tandem sequence using an optically active epoxide has been demonstrated.

摘要

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