Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amides

J Org Chem. 2005 Mar 18;70(6):2184-90. doi: 10.1021/jo0402780.

Abstract

[reaction: see text] Diverse organometallic reagents readily add to enantiopure N-sulfinyl beta-amino Weinreb amides providing the corresponding, stable, N-sulfinyl beta-amino carbonyl compounds in good to excellent yields. This new methodology represents a general solution to the problem of beta-amino carbonyl syntheses, which are important chiral building blocks and constituents of natural products. N-Sulfinyl beta-amino Weinreb amides are prepared by reaction of the potassium enolate of N-methoxy N-methylacetamide with sulfinimines (N-sulfinyl imines) or lithium N,O-dimethylhydroxylamine with N-sulfinyl beta-amino esters.

Publication types

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

MeSH terms

  • Aldehydes / chemical synthesis*
  • Amides / chemical synthesis
  • Amides / chemistry*
  • Ketones / chemical synthesis*
  • Molecular Conformation
  • Stereoisomerism
  • Sulfoxides / chemistry*

Substances

  • Aldehydes
  • Amides
  • Ketones
  • Sulfoxides