Direct asymmetric synthesis of beta-amino ketones from sulfinimines (N-sulfinylimines). Synthesis of (-)-indolizidine 209B

Org Lett. 2003 Dec 25;5(26):5011-4. doi: 10.1021/ol035981+.

Abstract

N-Sulfinyl beta-amino ketones, prepared directly from the potassium enolates of methyl ketones and enantiopure sulfinimines, are transformed in one pot to protected amino ketones, which are valuable chiral building blocks for the assembly of piperidines. The utility of this methodology is illustrated in a concise asymmetric synthesis of (-)-indolizidine 209B. [reaction: see text]

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Imines / chemical synthesis*
  • Indolizines / chemical synthesis*
  • Ketones / chemical synthesis*
  • Piperidines
  • Stereoisomerism

Substances

  • Alkaloids
  • Imines
  • Indolizines
  • Ketones
  • Piperidines
  • indolizidine 209B