An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes†,Chemical Science

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An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes†
Chemical Science ( IF 7.6 ) Pub Date : 2018-02-19 00:00:00 , DOI: 10.1039/c8sc00020d
Kevin X Rodriguez ₁ , Tara C Pilato ₁ , Brandon L Ashfeld ₁

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Enantioselective quaternary carbon construction in the assembly of cyclopentenones employing a Rh^II-catalyzed, formal [4+1]-cycloaddition is described. A Rh₂(S-TCPTTL)₄-catalyzed cyclopropanation of a vinyl ketene with a disubstituted diazo compound initiates a stereoretentive, accelerated ring expansion to provide the cycloadduct in good to excellent yields and enantioselectivity.

中文翻译：

一种不寻常的立体保留 1,3-季碳位移，导致重氮化合物和乙烯基烯酮之间发生对映选择性 RhII 催化的正式 [4+1]-环加成†

描述了采用 Rh ^II催化的正式 [4+1]-环加成反应组装环戊烯酮时的对映选择性季碳结构。Rh ₂ ( S -TCPTTL) ₄催化的乙烯基烯酮与二取代的重氮化合物的环丙烷化引发立构保留、加速环扩张，从而以良好至优异的产率和对映选择性提供环加合物。

更新日期：2018-02-19

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