1,3-Dipolar Cycloaddition Reactions of Imines of γ- and δ-Dialdehydes: Applications to the Synthesis of Novel Polyfunctional Pyrrolizidines and Indolizidines

Ronald Grigg; Simon Hargreves; James Redpath; Stefania Turchi; Gnanamoly Yoganathan

doi:10.1055/s-1999-3415

Synthesis 1999; 1999(3): 441-446
DOI: 10.1055/s-1999-3415

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1,3-Dipolar Cycloaddition Reactions of Imines of γ- and δ-Dialdehydes: Applications to the Synthesis of Novel Polyfunctional Pyrrolizidines and Indolizidines

Ronald Grigg^* , Simon Hargreves, James Redpath, Stefania Turchi, Gnanamoly Yoganathan

^*School of Chemistry, The University of Leeds, Leeds LS2 9JT, UK; Fax +44(1 13)2 33 65 01; E-mail: R.Grigg@chem.leeds.ac.uk

Abstract

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Combinations of imine → azomethine ylide → cycloaddition cascades with intramolecular reductive aminations mediated by sodium cyanoborohydride generates novel polyfunctional pyrrolizidines and indolizidines. The azomethine ylides are generated from imines of monoacetals of γ- and δ-dialdehydes via metal ion catalysis at ambient temperature.

cycloaddition - dialdehydes - reductive amination - pyrrolizidines - indolizidines

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