Highly enantioselective synthesis of pipecolic acid derivatives via an asymmetric aza-Diels-Alder reaction

Patrick D. Bailey, Derek J. Londesbrough, Timothy C. Hancox, John D. Heffernan, Andrew B. Holmes

Research output: Contribution to journalArticle

Abstract

Very high asymmetric induction is observed in the aza-Diels-Alder reaction between dienes and the imine (R)-PhMeCH-N=CHCO2PhMen* (where PhMen* = 8-phenylmenthyl), which bears matched auxiliaries on nitrogen and on the ester; reactions in trifluoroethanol, in the presence of trifluoroacetic acid (1 equiv.), give substituted pipecolic acid derivatives in ca 50% isolated yield, with only a single regio- and diastereo-isomer of the cycloadduct detectable in all cases (d.e.>95%).

Original languageEnglish
Pages (from-to)2543-2544
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number22
DOIs
Publication statusPublished - 1994

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