title: Stereocontrolled construction of seven-membered carbocycles using a combination of Brook rearrangement-mediated [3 + 4] annulation and epoxysilane rearrangement.
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.
authors.affiliation: Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8551, Japan.
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Nakai
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Kawahata
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Kei
authors.initials: K
authors.lastname: Takeda