Stereocontrolled synthesis of cyclopropanol amino acids from allylic sulfones: conformationally restricted building blocks

Org Lett. 2003 Oct 2;5(20):3687-90. doi: 10.1021/ol035451d.

Abstract

[reaction: see text] A new amino acid methyl ester with a cyclopropanol has been synthesized starting from the allyl sulfone 10. The starting material, 10, could be obtained in both enantiomeric forms. The stereoselectivity of the cyclopropane formation has been studied by molecular modeling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemistry*
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Ethers, Cyclic / chemistry*
  • Glutamic Acid / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism
  • Sulfones / chemistry*

Substances

  • Allyl Compounds
  • Amino Acids
  • Ethers, Cyclic
  • Sulfones
  • cyclopropanol
  • Glutamic Acid