Enantioselective Michael Addition of Aldehydes to β-Nitrostyrenes Catalyzed by (S)-N-(D-Prolyl)-1-triflicamido-3-phenylpropan-2-amine

被引：8
作者：
Gorde, Amol B. [1 ]
Ramapanicker, Ramesh [1 ,2 ]
机构：
[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
[2] Indian Inst Technol Kanpur, Ctr Environm Sci & Engn, Kanpur 208016, Uttar Pradesh, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 29期
关键词：
Michael addition; Organocatalysis; Aldehydes; Nitroalkenes; Enantioselectivity; ASYMMETRIC CATALYSIS; PHOSPHONIC ACID; EFFICIENT; KETONES; NITROALKENES; PEPTIDES; NITROOLEFINS; TRIPEPTIDES; WATER; FLOW;
D O I：
10.1002/ejoc.201900719
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new organocatalyst for the asymmetric Michael addition reaction of aldehydes with beta-nitrostyrenes is developed by coupling D-proline with (S)-1-triflicamido-3-phenylpropan-2-amine, which in turn is prepared from L-phenylalaninol. The Michael addition products were obtained in very high yields (up to 93 %) and with excellent enantioselectivity (up to 97 % ee) and high diastereoselectivity (up to >99:1 dr). The catalyst is effective for reactions between alpha-branched aldehydes and beta-nitrostyrenes.
引用
收藏
页码：4745 / 4751
页数：7
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