X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .43. METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES AND MENTHYL ACRYLATE

DA BARR, MJ DORRITY, R GRIGG, S HARGREAVES, JF MALONE, J MONTGOMERY, J REDPATH, P STEVENSON, M THORNTONPETT

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt(3) X-Ray crystal structures of representative cycloadducts establish that the absolute configuration of the newly established pyrrolidine stereocentres is independent of the metal salt and the size of the pyrrolidineC(2)-substituent for a series of aryl and aliphatic imines.

Original languageEnglish
Pages (from-to)273-294
Number of pages22
JournalTetrahedron
Volume51
Issue number1
Publication statusPublished - 02 Jan 1995

Keywords

  • CHIRAL AZOMETHINE YLIDES
  • ALPHA-AMINO ESTERS
  • CYCLO-ADDITION REACTIONS
  • DIELS-ALDER REACTIONS
  • DIASTEREOFACIAL SELECTIVITY
  • SYSTEMS
  • INDUCTION
  • PYRROLIDINES
  • GENERATION
  • MECHANISMS

Cite this