Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine

被引：86

作者：

Wang, M ^{[1
]}

Gao, LX ^{[1
]}

Mai, WP ^{[1
]}

Xia, AX ^{[1
]}

Wang, F ^{[1
]}

Zhang, SB ^{[1
]}

机构：

[1] Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 08期

关键词：

D O I：

10.1021/jo035719e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2874 / 2876

页数：3

共 28 条

[1] Thermodynamic vs supramolecular effects in the regiocontrol of the formation of new cyclotriphosphazene-containing chiral ligands with 1,1′-binaphthyl units:: Spiro vs ansa substitution at the N3P3 ring [J].