Suzuki-Miyaura 偶联/酸催化螺缩醛化两步一锅法合成苯并环化螺缩醛。

Two-step one-pot synthesis of benzoannulated spiroacetals by Suzuki-Miyaura coupling/acid-catalyzed spiroacetalization.

机构信息

Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.

出版信息

Org Lett. 2012 Oct 5;14(19):4998-5001. doi: 10.1021/ol302088w. Epub 2012 Sep 21.

DOI:10.1021/ol302088w

Abstract

Substituted benzoannulated spiroacetals were prepared from (2-haloaryl)alkyl alcohols and dihydropyranyl or dihydrofuranyl pinacol boronates using a Suzuki-Miyaura coupling followed by an acid-catalyzed spirocyclization. Application of the reaction to a glycal boronate provides an approach to annulated spiroacetals in enantiopure form.

摘要

取代的苯并稠合螺缩醛是通过（2-卤代芳基）烷基醇与二氢吡喃基或二氢呋喃基频哪醇硼酸酯的铃木-宫浦偶联反应，然后进行酸催化的螺环化反应制备的。该反应在糖醛硼酸酯中的应用为非对映纯形式的稠合螺缩醛提供了一种方法。