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Efficient desymmetrisation of a meso-imide using a chiral oxazaborolidine catalyst

Lookup NU author(s): Rachel Dixon

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Abstract

Desymmetrisation of a meso-imide by enantioselective reduction using a chiral oxazaborolidine catalyst derived from (1R,2S)-cis-1-amino-2-indanol followed by reduction of the hydroxylactam product proceeded with good enantiomeric excess (80-91%) at significantly lower catalyst loadings compared to reactions using the prolinol-derived catalyst. Models for the selectivity observed are proposed based upon structural probes and experimental observations. (C) 2002 Elsevier Science Ltd. All rights reserved.

Publication metadata

Author(s): Dixon RA, Jones S

Publication type: Article

Publication status: Published

Journal: Tetrahedron: Asymmetry

Year: 2002

Volume: 13

Issue: 10

Pages: 1115-1119

ISSN (print): 0957-4166

ISSN (electronic): 1362-511X

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/S0957-4166(02)00248-3

DOI: 10.1016/S0957-4166(02)00248-3

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