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对映富集合成具有季立体中心的环丙烯,多功能构建块。

Enantioenriched synthesis of cyclopropenes with a quaternary stereocenter, versatile building blocks.

机构信息

Department of Chemistry, Faculty of Science, Graduate School, and Institute for Advanced Study, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.

出版信息

J Am Chem Soc. 2011 Jan 19;133(2):170-1. doi: 10.1021/ja1089217. Epub 2010 Oct 29.

Abstract

Ir(salen) complexes were found to catalyze enantioselective cyclopropenation efficiently. Cyclopropenation can be carried out using either a donor/acceptor- or an acceptor/acceptor-substituted diazo compound such as α-aryl-α-diazoacetates, α-phenyl-α-diazophosphonate, 2,2,2-trifluoro-1-phenyl-1-diazoethane, and α-cyano-α-diazoacetamide as carbenoid precursors. The reactions provide highly enantioenriched cyclopropenes (84-98% ee) with a functionalized quaternary carbon as versatile building blocks.

摘要

手性(席夫碱)配合物被发现能够有效地催化对映选择性环丙烯化反应。环丙烯化反应可以使用供体/受体取代或受体/受体取代的重氮化合物作为碳烯前体进行,例如α-芳基-α-二氮乙酸酯、α-苯基-α-二氮膦酸酯、2,2,2-三氟-1-苯基-1-重氮乙烷和α-氰基-α-二氮乙酰胺。这些反应提供了高度对映富集的环丙烯(84-98%ee),具有作为多功能构建块的官能化季碳。

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