The use of the aza-Diels-Alder reaction in the synthesis of pinidine and other piperidine alkaloids

Patrick D. Bailey, Peter D. Smith, Keith M. Morgan, Georgina M. Rosair

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The imine Ph2CHN=CHCO2Et, generated from benzhydrylamine and ethyl glyoxylate, provides a Diels-Alder adduct with 1,3-pentadiene from which a range of cis-2,6-disubstituted piperidines can be accessed; the benzhydryl group confers high diastereocontrol for derivatising the six-membered ring, allowing access to 2,5,6-trisubstituted piperidines, and to 2,6-disubstituted piperidines such as pinidine. © 2002 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1071-1074
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number6
DOIs
Publication statusPublished - 4 Feb 2002

Keywords

  • Alkaloids
  • Diels-Alder reaction
  • Piperidines

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