X-Y-ZH Systems as potential 1,3-dipoles. Part 151 1 Part 14. R. Grigg, H.Q.N. Gunaratne and V. Sridharan, Tetrahedron, 1987, 43, 5887.. Amine generated azaallyl anios versus metallo-1,3-dipoles in cycloadditions of α-amino acid esters. Facile regio- and stereo-specific formation of pyrrolidines

Darrin A. Barr*, Ronald Grigg, H. Q.Nimal Gunaratne, James Kemp, Peter McMeekin, Visuvanathar Sridharan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

116 Citations (Scopus)

Abstract

Kinetic studies of the deprotonation of arylidene imines of alanine and phenylglycine esters by tertiary amines and pyridine and cycloaddition of the resultant 4π-azaallyl anions to N-phenylmaleimide show the expected dependance on the p-substituent in the aryl ring. e.g. p-NO2 > H > OMe >fs NMe2. A combination of metal salt (silver, lithium. or zinc) and triethylamine in THF, dipolar aprotic solvents (MeCN, DMSO, DMF) or N-methylacetamide effects regio- and stereo-specific or highly stereo-selective inter- and intra-molecular cycloaddition of imines of phenylglycine. alanine and glycine esters to a range of dipolarophiles probably via metallo-1,3-dipole formation at room temperature. Silver acetate is a more efficient and selective catalyst than lithium bromide and reactions in acetonitrile, DMSO or N-methylacetamide, are especially rapid (O.1-3.5h).

Original languageEnglish
Pages (from-to)557-570
Number of pages14
JournalTetrahedron
Volume44
Issue number2
DOIs
Publication statusPublished - 1988

Bibliographical note

Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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