Catalytic enantioselective Michael addition of deconjugated butyrolactams to maleimides

被引：10
|
作者：
Ray, Bidisha [1 ]
Mukherjee, Santanu [1 ]
机构：
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
来源：
TETRAHEDRON | 2019年 / 75卷 / 24期
关键词：
Michael addition; Butyrolactam; Maleimide; All-carbon quaternary stereocenter; Bifunctional catalysis; GAMMA-SUBSTITUTED BUTENOLIDES; CHIRAL BICYCLIC GUANIDINE; DIELS-ALDER REACTIONS; CONJUGATE ADDITION; ASYMMETRIC CONSTRUCTION; 1,3-DIPOLAR CYCLOADDITION; 1,3-DICARBONYL COMPOUNDS; EFFICIENT CONSTRUCTION; AZOMETHINE YLIDES; ARYLBORONIC ACIDS;
D O I：
10.1016/j.tet.2019.04.049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first catalytic enantioselective Michael addition of deconjugated butyrolactams to N-arylmaleimides is developed with the help of a bifunctional tertiary aminosquaramide catalyst. Unlike the widely explored and structurally related vinylogous nucleophile - deconjugated butenolides, deconjugated butyrolactams are found to be exclusively alpha-selective. The resulting highly substituted and densely functionalized products, bearing contiguous all-carbon quaternary and tertiary stereocenters, are formed in good yields with moderate diastereoselectivity and good to excellent enantioselectivity (up to 99:1 er). (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3292 / 3298
页数：7
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