X=Y-ZH compounds as potential 1,3-dipoles. Part 64: Synthesis of highly substituted conformationally restricted and spiro nitropyrrolidines via Ag(I) catalysed azomethine ylide cycloadditions

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Grigg R., Kilner C., Sarker M. A. B., de la Cierva C. O., DÖNDAŞ H. A.

TETRAHEDRON, vol.64, no.37, pp.8974-8991, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 64 Issue: 37
  • Publication Date: 2008
  • Doi Number: 10.1016/j.tet.2008.05.132
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.8974-8991
  • Keywords: metallo-azomethine ylides, cycloaddition, silver oxide, nitroolefins, pyrrolidines, spirocycles, AZA-CEPHALOTAXINE SKELETON, IN-SITU GENERATION, STEREOSELECTIVE PREPARATION, ANTIPSYCHOTIC AGENTS, ANALOGS, NITRO, STEREOCHEMISTRY, DERIVATIVES, DOPAMINE, SYSTEMS
  • Çukurova University Affiliated: No

Abstract

13-Dipolar reactions of imines of both acyclic and cyclic alpha-amino esters with a range of nitroolefins using a combination of AgOAc or Ag(2)O with NEt(3) are described. In most cases the reactions were highly regio and stereospecific and endo-cycloadducts were obtained in good yield. However, in a few cases the initially formed cycloadducts underwent base catalysed epimerisation. The stereochemistry of the cycloadducts was assigned from NOE data and established unequivocally in several cases by X-ray crystallography. (C) 2008 Elsevier Ltd. All Fights reserved.