Organocatalytic Michael addition of aldehydes to trisubstituted nitroolefins

被引：19
|
作者：
Wang, Leilei [1 ]
Zhang, Xiaojing [1 ]
Ma, Dawei [2 ]
机构：
[1] Shenyang Pharmaceut Univ, Shenyang 110016, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 37期
基金：
中国国家自然科学基金;
关键词：
Organocatalysis; Michael addition; Nitroolefins; ENANTIOSELECTIVE MICHAEL; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; EFFICIENT; NITROALKENES; CATALYSIS; KETONES; ETHERS; ROUTE; WATER;
D O I：
10.1016/j.tet.2012.05.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The combination of O-TMS protected diphenyl-prolinol and benzoic acid was found to be effective to catalyze the Michael addition of aldehydes to 3-substituted 3-nitroacrylates. The reaction provided syn,anti-Michael adducts with good diastereoselectivity and excellent enantioselectivity. Some beta-aryl and alpha-methyl substituted nitroolefins also worked under these conditions, although prolonging reaction time was required. These adducts could be used for assembling 2,3,4-trisubstituted pyrrolidines through simple hydrogenation. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7675 / 7679
页数：5
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