受热能引发的给体/受体卡宾环加成反应。

Thermally induced cycloadditions of donor/acceptor carbenes.

机构信息

Emory University, Department of Chemistry, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.

出版信息

Org Lett. 2011 Aug 19;13(16):4284-7. doi: 10.1021/ol201628d. Epub 2011 Jul 18.

DOI:10.1021/ol201628d

Abstract

The thermal decomposition of aryldiazoacetates and aryldiazoketones in the absence of a catalyst leads to synthetically useful transformations. The thermal reaction of aryldiazoacetates with alkenes generates cyclopropanes in 68-97% yield and with good diastereoselectivity (up to 19:1 dr) when the aryl substituent is electron-rich. The thermal reaction of aryldiazoketones with alkenes generated cyclobutanones in 71-94% yield and with good diastereocontrol (≥9:1 dr).

摘要

芳基重氮乙酸酯和芳基重氮酮在没有催化剂的情况下热分解会导致具有合成用途的转化。芳基重氮乙酸酯与烯烃的热反应在芳基取代基为富电子时以 68-97%的产率和良好的非对映选择性（高达 19:1 dr）生成环丙烷。芳基二氮烯酮与烯烃的热反应以 71-94%的产率和良好的非对映控制（≥9:1 dr）生成环丁酮。