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Synlett 1996; 1996(9): 853-855
DOI: 10.1055/s-1996-5598
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Synthesis of Functionalised Azabicycles via a Regiospecific Intramolecular Aldol Reaction

Robert A. Stockman, Peter Szeto, Stephen H. J. Thompson, Michael S. Hadley, David C. Lathbury, Timothy Gallagher*
  • *School of Chemistry, University of Bristol, Bristol BS8 1TS U.K.
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Publication Date:
31 December 2000 (online)

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A series of ketoaldehydes (1) undergo aldol-type cyclisation in the presence of a secondary amine to give the azabicyclic enones (2). Optimal reaction conditions involve use of 2,2,6,6-tetramethylpiperidine followed by silica gel, and participation of an electrophilic iminium species is suggested.

Aldol cyclisation - azabicycles - indolizidines

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