Regioselectivity and diastereoselectivity in the indium-mediated homoallyl-cyclopropanation of dibenzylidene acetone (dba)

SM Capps, GC Lloyd-Jones*, M Murray, TM Peakman, KE Walsh

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Indium mediated reaction of dibenzylidene acetone (dba) with [H-2(2)]-allyl bromide affords 1,1-distyryl-2-(but-3-enyl) cyclopropane 7 (a triene) as a mixture of four isotopomers. Whilst this reaction is not regiospecific, the analogous reaction employing crotyl bromide in place of allyl bromide is highly regioselective and somewhat selective for the cis cyclopropane isomer. When the reaction is performed with dimethylallyl bromide, cyclopropanation fails and tetraene products are obtained instead. (C) 1998 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2853-2856
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number18
Publication statusPublished - 30 Apr 1998

Keywords / Materials (for Non-textual outputs)

  • AQUEOUS-MEDIA
  • ALLYLIC HALIDES
  • ALLYLATION
  • ALKYLATION
  • CHEMISTRY
  • REAGENTS

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