Synthesis of new mono-N-tosylated diamine ligands based on (R)-(+)-limonene and their application in asymmetric transfer hydrogenation of ketones and imines

被引：27
|
作者：
Roszkowski, Piotr [1 ]
Maurin, Jan K. [2 ,3 ]
Czarnocki, Zbigniew [1 ]
机构：
[1] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland
[2] Natl Med Inst, PL-00725 Warsaw, Poland
[3] Natl Ctr Nucl Res, PL-05400 Otwock, Poland
来源：
TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 11期
关键词：
LIMONENE OXIDE; CHIRAL AUXILIARIES; KINETIC SEPARATION; AMINO-ALCOHOLS; COMPLEXES; ALDEHYDES; CATALYSTS; DIETHYLZINC; DERIVATIVES; AZIRIDINES;
D O I：
10.1016/j.tetasy.2013.04.010
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A synthetic procedure leading to the preparation of a new family of enantiopure mono-N-tosylated-1,2-diamines derived from (R)-(+)-limonene is described. (+)-Limonene was transformed into the appropriate N-tosyl derivative using N-tosylaziridination based on chloramine-T trihydrate. Subsequent ring opening by sodium azide afforded the corresponding isomeric azides. Finally, reduction of the azide function gave enantiomerically pure mono-N-tosylated-1,2-diamines. The ligands obtained proved to be effective in the asymmetric transfer hydrogenation protocol on aromatic ketones and imines. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：643 / 650
页数：8
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