Asymmetric construction of three contiguous stereogenic centers by conjugate addition-alkylation of lithium ester enolate

Org Lett. 2009 May 7;11(9):2007-9. doi: 10.1021/ol900447n.

Abstract

A chiral ligand- and lithium amide-assisted asymmetric conjugate addition of lithium enolate of propionate to cyclopentenecarboxylate gave the corresponding lithium enolate, whose allylation gave the key intermediate of the marine alkaloid halichlorine as a single diastereomer with moderate enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkylation
  • Catalysis
  • Esters
  • Lithium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Esters
  • Organometallic Compounds
  • Spiro Compounds
  • halichlorine
  • Lithium