Transition-Metal-Free Reactions of Boronic Acids: 1,3-Stereochemical Induction in the Substrate-Controlled Conjugate Addition

被引:12
|
作者
Roscales, Silvia [1 ]
Ortega, Victor [1 ]
Csaky, Aurelio G. [1 ]
机构
[1] Univ Complutense, Inst Pluridisciplinar, E-28040 Madrid, Spain
来源
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 24期
关键词
ASYMMETRIC MICHAEL ADDITION; STEREOSELECTIVE-SYNTHESIS; ALKENYLBORONIC ACIDS; BIOLOGICAL-ACTIVITY; CARBOXYLIC-ACIDS; TETRAHYDROPYRANS; 1,4-ADDITION; KETONES; ENONES; ALKENYLATION;
D O I
10.1021/jo402262m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The substrate-controlled 1,3-stereoselective conjugate addition of boronic acids and potassium trifluoroborates under metal-free conditions has been developed. This reaction affords bicyclic acetals, which have been used as key intermediates in the stereodivergent synthesis of polysubstituted tetrahydropyrans.
引用
收藏
页码:12825 / 12830
页数:6
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