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TitleEfficient desymmetrisation of a meso-imide using a chiral oxazaborolidine catalyst
Publication TypeJournal Article
Year of Publication2002
AuthorsDixon, R.A., and Jones S.
JournalTetrahedron Asymmetry
Pagination1115 - 1119
Date Published2002
ISSN09574166 (ISSN)
Keywords1 amino 2 indanol, alcohol derivative, article, catalyst, chemical reaction, enantioselectivity, high performance liquid chromatography, imide, infrared spectrometry, Mass spectrometry, oxazaborolidine derivative, priority journal, unclassified drug
AbstractDesymmetrisation 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. © 2002 Elsevier Science Ltd. All rights reserved.

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