Efficient synthesis of α-tertiary α-silylamines from aryl sulfonylimidates via one-pot, sequential C-Si/C-C bond formations

Org Lett. 2012 Jun 1;14(11):2906-9. doi: 10.1021/ol301194e. Epub 2012 May 23.

Abstract

An efficient and flexible route for the synthesis of α-tertiary (α,α-dibranched) α-silylamines via sequential reactions of sulfonylimidates using readily available phenyldimethylsilyllithium and Grignard reagents is described. The procedure allows successive formation of C-Si/C-C bonds in a single flask.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry
  • Catalysis
  • Indicators and Reagents
  • Lithium / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Organosilicon Compounds / chemical synthesis*
  • Organosilicon Compounds / chemistry
  • Stereoisomerism
  • Sulfones / chemistry*

Substances

  • Amines
  • Indicators and Reagents
  • Organometallic Compounds
  • Organosilicon Compounds
  • Sulfones
  • phenyldimethylsilyllithium
  • Lithium