Application of catalytic dynamic resolution of N-Boc-2-lithiopiperidine to the asymmetric synthesis of 2-aryl and 2-vinyl piperidines

Org Lett. 2011 Feb 4;13(3):394-7. doi: 10.1021/ol102682r. Epub 2010 Dec 21.

Abstract

The highly enantioselective synthesis of 2-aryl- and 2-vinyl-piperidines has been accomplished through a catalytic dynamic resolution (CDR) of N-Boc-2-lithiopiperidine. The method has been applied to the synthesis of both enantiomers of the tobacco alkaloid anabasine.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Anabasine / chemical synthesis*
  • Anabasine / chemistry
  • Catalysis
  • Molecular Structure
  • Nicotiana / chemistry
  • Organometallic Compounds / chemistry*
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Stereoisomerism
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry

Substances

  • Alkaloids
  • N-Boc-2-lithiopiperidine
  • Organometallic Compounds
  • Piperidines
  • Vinyl Compounds
  • Anabasine