通过迈克尔引发的环闭合反应，可直接且高非对映选择性地获得官能化的单氟化环丙烷。

A straightforward and highly diastereoselective access to functionalized monofluorinated cyclopropanes via a Michael initiated ring closure reaction.

机构信息

Normandie Université, COBRA, UMR 6014 et FR 3038; Université de Rouen; INSA Rouen; CNRS , 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex, France.

出版信息

Org Lett. 2013 Nov 1;15(21):5598-601. doi: 10.1021/ol402837u. Epub 2013 Oct 18.

DOI:10.1021/ol402837u

PMID:24138105

Abstract

The synthesis of highly functionalized monofluorinated cyclopropanes based on a Michael Initiated Ring Closure (MIRC) reaction has been developed. The addition of quaternary ammonium salts derived from ethyl bromofluoroacetate on a panel of electron deficient alkenes followed by cyclization gave rise to an efficient access to monofluorinated cyclopropanes with good yields and remarkable diastereoselectivity.

摘要

基于迈克尔加成引发的闭环（MIRC）反应，开发了高效合成高官能化单氟环丙烷的方法。一系列缺电子烯烃与乙基溴代氟乙酸酯衍生的季铵盐加成，随后闭环反应，以良好的收率和显著的非对映选择性得到了单氟环丙烷。