由辛可尼定衍生的手性季铵盐催化的对映选择性碘内酯化反应。

Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.

作者信息

Wang Mang, Gao Lian Xun, Mai Wen Peng, Xia Ai Xiang, Wang Fang, Zhang Suo Bo

机构信息

State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Science, Changchun, 130022, P. R. China.

出版信息

J Org Chem. 2004 Apr 16;69(8):2874-6. doi: 10.1021/jo035719e.

DOI:10.1021/jo035719e

PMID:15074944

Abstract

Chiral quaternary ammonium salts derived from cinchonidine have been applied to catalyze the stereoselective iodolactonizations of trans-5-aryl-4-pentenoic acids leading to a mixture of two regioselectively iodolactonized products with fair to excellent yield (37-98%) and moderate enantioselectivity (exo = 42.0% ee, endo = 31.0% ee) under mild conditions. This work is the first example of asymmetric iodolactonization reaction in the presence of less than a stoichiometric amount of chiral reagent.

摘要

源自辛可尼定的手性季铵盐已被用于催化反式-5-芳基-4-戊烯酸的立体选择性碘内酯化反应，在温和条件下生成两种区域选择性碘内酯化产物的混合物，产率良好至优异（37-98%），对映选择性适中（外型 = 42.0% ee，内型 = 31.0% ee）。这项工作是在化学计量比以下的手性试剂存在下进行不对称碘内酯化反应的首个实例。