Stereoselective synthesis of trifluoromethyl-substituted 1,2-diamines by aza-Michael reaction with trans-3,3,3-trifluoro-1-nitropropene

被引：22

作者：

Turconi, Joel

Lebeau, Luc

Paris, Jean-Marc

Mioskowski, Charles

机构：

[1] Univ Louis Pasteur Strasbourg 1, Fac Pharm, Lab Synthese Bioorgan Associe CNRS, F-67401 Illkirch Graffenstaden, France

[2] Rhone Poulenc Rech, Ctr Rech & Technol Lyon, F-69192 St Fons, France

来源：

TETRAHEDRON | 2006年 / 62卷 / 34期

关键词：

perfluoroalkyl nitroalkene; diastereoselective aza-Michael addition; 3,3,3-trifluoro-1-nitropropene; 4-phenyl-2-oxazolidinone;

D O I：

10.1016/j.tet.2006.06.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aza-Michael addition of optically pure 4-phenyl-2-oxazolidinone to 3,3,3-trifluoro-1-nitropropene proceeds smoothly at low temperature with a high yield. Diastereoselectivity of the addition depends on the base used and lithiated species proved to be highly efficient affording 92% de. Optically pure 1,2-diamino-3,3,3-trifluoropropane is prepared in 58% yield from the aza-Michael addition product through a three-step procedure. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8109 / 8114

页数：6