Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes

被引：13

作者：

Guang, Jie ^{[1
]}

Zhao, John Cong-Gui ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 42期

关键词：

Michael reaction; Organocatalysis; alpha-Ketophosphonate; Nitroalkene; Enantioselective; Amide surrogate; ENANTIOSELECTIVE 1,4-ADDITION REACTIONS; DIRECT CONJUGATE ADDITION; DIPHENYL PHOSPHITE; 1,3-DICARBONYL COMPOUNDS; 3-SUBSTITUTED OXINDOLES; UNACTIVATED KETONES; ALDOL REACTION; NITROOLEFINS; SQUARAMIDE; EQUIVALENTS;

D O I：

10.1016/j.tetlet.2013.08.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective Michael reaction of beta-aryl-alpha-ketophosphonates and nitroalkenes has been realized by using a new bifunctional Takemoto-type thiourea catalyst. The primary Michael adducts obtained were converted in situ to the corresponding amides through the aminolysis. High yields, excellent diaste-reoselectivities (>95:5 dr), and good enantioselectivities (up to 81% ee) have been achieved for the corresponding oc,13-disubstituted gamma-nitroamides. This reaction again demonstrated that alpha-ketophosphonates are interesting pronucleophiles that can be used as amide surrogates in organocatalyzed reactions. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5703 / 5706

页数：4

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