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

Lookup NU author(s): Rachel Dixon, Dr Simon Jones

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Abstract

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 hydroxylactam product to give the γ-lactam. The enantiomeric excesses were shown to be 27-99% by chiral HPLC and chiral GC of the γ-lactam products with the nitrogen substituent playing a pivotal role in determining yield and selectivity. © 2006 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Barker MD, Dixon RA, Jones S, Marsh BJ

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2006

Volume: 62

Issue: 50

Pages: 11663-11669

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/j.tet.2006.09.051

DOI: 10.1016/j.tet.2006.09.051

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