Practical and stereoselective synthesis of β-amino sulfones from alkyl phenyl sulfones and N-(tert-butylsulfinyl) aldimines

Org Biomol Chem. 2011 Oct 7;9(19):6502-5. doi: 10.1039/c1ob05992k. Epub 2011 Aug 22.

Abstract

A practical and straightforward approach for the highly stereoselective synthesis of β-amino sulfones was developed. With lithium bis(trimethylsilyl)amide as the base, the corresponding sulfone-stabilized carbanion derived from alkylphenyl sulfone can be transferred to N-(tert-butylsulfinyl) aldimines in excellent yields and with high diastereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic
  • Crystallography, X-Ray
  • Imines / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry*

Substances

  • Imines
  • Sulfones