Stereocontrolled Construction of Seven-Membered Carbocycles Using a Combination of Brook Rearrangement-Mediated [3 + 4] Annulation and Epoxysilane Rearrangement

Stereocontrolled Construction of Seven-Membered Carbocycles Using a Combination of Brook Rearrangement-Mediated [3 + 4] Annulation and Epoxysilane Rearrangement

Reactions of δ-silyl-γ,δ-epoxy-α,β-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 a...

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Veröffentlicht in:Journal of organic chemistry 2007-02, Vol.72 (4), p.1379-1387
Hauptverfasser: Nakai, Yoshio, Kawahata, Masatoshi, Yamaguchi, Kentaro, Takeda, Kei
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Organic chemistry
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container_end_page 1387
container_issue 4
container_start_page 1379
container_title Journal of organic chemistry
container_volume 72
creator Nakai, Yoshio
Kawahata, Masatoshi
Yamaguchi, Kentaro
Takeda, Kei
description Reactions of δ-silyl-γ,δ-epoxy-α,β-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.
doi_str_mv 10.1021/jo062282c
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Exact sciences and technology
Organic chemistry
title Stereocontrolled Construction of Seven-Membered Carbocycles Using a Combination of Brook Rearrangement-Mediated [3 + 4] Annulation and Epoxysilane Rearrangement
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