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Review | Regular issue | Vol 78, No. 12, 2009, pp.2919-2941
Published online, 14th October, 2009
DOI: 10.3987/REV-09-657
Development of Epoxysilane Rearrangement and Its Application to Chirality Transfer

Michiko Sasaki, Hidaka Ikemoto, and Kei Takeda*

*Divison of Medicinal Chemisry, Graduate School of Biomedical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan

Abstract

Development and synthetic application of epoxysilane rearrangement, a novel synthetic use of α,β-epoxysilanes, in which an anion-induced ring-opening of epoxide and Brook rearrangement in the resulting α-silyl alkoxide occur in a tandem fashion to provide a β-siloxy allyl anion, are described. Chirality transfer from epoxides to the position next to a nitrile group by taking advantage of the concerted process of the rearrangement is also reported.