The role of acyloxyphosphonium ions and the stereochemical influence of base in the phosphorane-mediated esterification of alcohols

被引：55
作者：
McNulty, J
Capretta, A
Laritchev, V
Dyck, J
Robertson, AJ
机构：
[1] McMaster Univ, Dept Chem, Hamilton, ON L8S 4M1, Canada
[2] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada
[3] Cytec Canada Inc, Niagara Falls, ON L2E 6T4, Canada
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 34期
关键词：
acylation; amines; peroxides; phosphanes; synthetic methods;
D O I：
10.1002/anie.200351209
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Intimate details of the Mitsunobu mechanism: The trapping of an acyloxytributylphosphonium ion with a chiral secondary alcohol leads to either retention or inversion of stereochemistry in the resulting ester depending on the exclusion or inclusion of a base (see scheme). Insight into the mechanism of phosphorane-mediated esterification processes is presented.
引用
收藏
页码：4051 / 4054
页数：4
相关论文
共 26 条
123