Stereoselective construction of a 5-aza-spiro[2,4]heptane motif via catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides and ethyl cyclopropylidene acetate

Chem Commun (Camb). 2011 Mar 7;47(9):2616-8. doi: 10.1039/c0cc04329j. Epub 2011 Jan 14.

Abstract

A direct and facile synthesis of highly functional 5-aza-spiro[2,4]heptanes, a valuable structural motif for drug discovery, is developed via catalytic asymmetric 1,3-dipolar cycloaddition of cyclopropylidene acetate and azomethine ylides for the first time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Azo Compounds / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Heptanes / chemical synthesis
  • Heptanes / chemistry*
  • Molecular Conformation
  • Spiro Compounds / chemistry*
  • Stereoisomerism
  • Thiosemicarbazones / chemistry*

Substances

  • Aza Compounds
  • Azo Compounds
  • Heptanes
  • Spiro Compounds
  • Thiosemicarbazones
  • azomethine