Organocatalytic Mitsunobu reactions

被引：129
|
作者：
Sze But, Tracy Yuen [1 ]
Toy, Patrick H. [1 ]
机构：
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 30期
关键词：
D O I：
10.1021/ja063141v
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A catalytic Mitsunobu reaction system is described in which the azo reagent is used as an organocatalyst and iodosobenzene diacetate is used as the stoichiometric oxidant. In this system, iodosobenzene diacetate oxidizes the formed hydrazine byproduct to regenerate the azo reagent. Yields obtained in the catalytic reactions using a variety of carboxylic acids and alcohols were slightly lower than those obtained from corresponding stoichiometric reactions. Both primary and secondary alcohols can be used as substrates in this reaction system, with the secondary alcohols affording products with inverted stereochemistry at the carbinol center. Copyright © 2006 American Chemical Society.
引用
收藏
页码：9636 / 9637
页数：2
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