The crucial role of the nitrogen substituent in the desymmetrisation of cyclic meso-imides using B-Me and B-OMe oxazaborolidine catalysts

被引：13

作者：

Barker, Mike D.

Dixon, Rachel A.

Jones, Simon

Marsh, Barrie J.

机构：

[1] Newcastle Univ, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

[2] GlaxoSmithKline Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

[3] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

TETRAHEDRON | 2006年 / 62卷 / 50期

关键词：

asymmetric reduction; oxazaborolidine; catalysis; imides;

D O I：

10.1016/j.tet.2006.09.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various cyclic meso-imides have been desymmetrised via enantioselective reduction using two chiral oxazaborolidine catalysts derived from (1R,2S)-cis-1-amino-indan-2-ol followed by the reduction of the hydroxylactarn product to give the gamma-lactam. The enantiomeric excesses were shown to be 27-99% by chiral HPLC and chiral GC of the gamma-lactam products with the nitrogen substituent playing a pivotal role in determining yield and selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

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收藏

页码：11663 / 11669

页数：7

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