Stereoselectivity in the rhodium(II) acetate catalysed cyclopropanations of 2-diazo-1-indanone with styrenes

William Bauta, John Harold Dodd, James Bullington, Diane Gauthier, Gregory Leo, Patricia McDonnell

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16 Scopus citations

Abstract

The rhodium(II) acetate catalysed cyclopropanation reactions of 2- diazo-1-indanone 4 with various substituted styrenes 5 have been investigated. The cyclopropane diastereomer 6a bearing a trans relationship between the carbonyl and the aryl ring was in all cases the predominant isomer and the ratio of stereoisomers almost constant over a range of styrene substituents. Styrenes bearing electron-donating substituents gave slightly better stereoselectivity in favour of the trans isomer. These results are substantiated by a mechanistic proposal. (C) 2000 Published by Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)1491-1494
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number10
DOIs
StatePublished - Mar 4 2000

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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