Synlett 1989; 1989(1): 38-40
DOI: 10.1055/s-1989-34709
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Lewis Acid-Induced π-Cyclization of Glycine-Cation Equivalents to Substituted Pipecolic Acid Derivatives

Peter M. Esch* , Ilona M. Boska, Henk Hiemstra, W. Nico Speckamp
  • *Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands
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Publication History

Publication Date:
26 February 2002 (online)

Intramolecular reactions of glycine-cation equivalents with simple olefins, induced by SnCl4, lead to pipecolic acid derivatives. A bicyclic dioxonium ion is proposed as the crucial intermediate in these reactions, which mainly lead to either cis-4-hydroxy- or trans-4-chloropipecolic esters, dependent on the work-up conditions. A bicyclie (indolizidine) and tricyclic skeleton are also readily accessible.