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TitleThe crucial role of the nitrogen substituent in the desymmetrisation of cyclic meso-imides using B-Me and B-OMe oxazaborolidine catalysts
Publication TypeJournal Article
Year of Publication2006
AuthorsBarker, M.D., Dixon R.A., Jones S., and Marsh B.J.
Pagination11663 - 11669
Date Published2006
ISSN00404020 (ISSN)
Keywordsarticle, catalysis, enantioselectivity, high performance liquid chromatography, imide, priority journal, Reduction, substitution reaction
AbstractVarious 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.

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