Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol

被引：76
|
作者：
Trost, Barry M. [1 ]
Gnanamani, Elumalai [1 ]
Kalnmals, Christopher A. [1 ]
Hung, Chao-I Joey [1 ]
Tracy, Jacob S. [1 ]
机构：
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 04期
关键词：
MICHAEL ADDITION;
D O I：
10.1021/jacs.8b13367
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report the first enantio- and diaster-eoselective 1,4-addition of butenolides to chromones. Both alpha,beta- and beta,gamma-butenolide nucleophiles are compatible with the Zn-ProPhenol catalyst, and preactivation as the siloxyfurans is not required. The scope of electrophiles includes a variety of substituted chromones, as well as a thiochromone and a quinolone, and the resulting vinylogous addition products are generated in good yield (31 to 98%), diastereo- (3:1 to >30:1), and enantioselectivity (90:10 to 99:1 er). These Michael adducts allow rapid access to several natural product analogs, and can be easily transformed into a variety of other interesting scaffolds as well.
引用
收藏
页码：1489 / 1493
页数：5
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