Cycloaddition of chiral tert-butanesulfinimines with trimethylenemethane

Org Lett. 2013 Apr 19;15(8):2030-3. doi: 10.1021/ol400720b. Epub 2013 Apr 4.

Abstract

The cycloaddition of chiral tert-butanesulfinimines with trimethylenemethane is found to give facile access to methylene-pyrrolidines with good yields and diastereoselectivities. The full scope of the cycloaddition is explored, and a range of transformations of the formed methylenepyrrolidines to give a range of functionalized chiral pyrrolidines is presented.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butanes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cycloaddition Reaction
  • Imines / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Stereoisomerism
  • Sulfonium Compounds / chemistry*

Substances

  • Butanes
  • Imines
  • Pyrrolidines
  • Sulfonium Compounds
  • sulfinimine
  • trimethylenemethane
  • Methane