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氯乙酸酯和α-氯代乙酰胺烯醇化物共轭加成产生的碳负离子引发的环氧硅烷重排：官能化环丙烷衍生物的形成

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

作者信息

Okamoto Noriko, Sasaki Michiko, 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 734-8553, Japan.

出版信息

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

DOI:10.1021/ol060469k
PMID:16623577
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.

摘要

[反应：见正文] 在α-位带有环氧硅烷部分的烯酸酯与2-氯乙酰胺的烯醇锂反应，通过包括迈克尔加成、环氧化物开环、布鲁克重排和分子内烷基化的串联过程，得到了高度官能化的环丙烷衍生物。

相似文献

1
Epoxysilane rearrangement induced by a carbanion generated by conjugate addition of enolates of chloroacetate and alpha-chloroacetamides: formation of functionalized cyclopropane derivatives.氯乙酸酯和α-氯代乙酰胺烯醇化物共轭加成产生的碳负离子引发的环氧硅烷重排：官能化环丙烷衍生物的形成
Org Lett. 2006 Apr 27;8(9):1889-91. doi: 10.1021/ol060469k.
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Nitrile anion cyclization with epoxysilanes followed by Brook rearrangement/ring-opening of cyclopropane nitriles/alkylation.腈基阴离子与环氧硅烷环化，随后进行布鲁克重排/环丙烷腈的开环/烷基化反应。
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[Development and synthetic application of epoxysilane rearrangement].[环氧硅烷重排的发展与合成应用]
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[Development of new synthetic reactions featuring tandem carbon-carbon bond formation].[具有串联碳-碳键形成的新型合成反应的开发]
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Stereocontrolled construction of seven-membered carbocycles using a combination of Brook rearrangement-mediated [3 + 4] annulation and epoxysilane rearrangement.
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Nitrile anion cyclization with epoxysilanes followed by brook rearrangement/ring opening of cyclopropane nitriles/alkylation.腈基阴离子与环氧硅烷环化，随后进行布鲁克重排/环丙烷腈的开环/烷基化反应。
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Highly diastereoselective formation of 1,2,3-trisubstituted cyclopropane derivatives.1,2,3-三取代环丙烷衍生物的高非对映选择性形成。
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Formation of functionalized carbocycles via base-promoted ring opening/Brook rearrangement/allylic alkylation of gamma-silyl-beta,gamma-epoxybutanenitrile followed by nitrile anion cyclization with bis-electrophiles.通过碱促进的γ-硅基-β,γ-环氧丁腈的开环/布鲁克重排/烯丙基烷基化，随后腈阴离子与双亲电试剂进行环化反应，形成官能化碳环。
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