Nonenzymatic enantioselective monoacetylation of prochiral 2-protectedamino-2-alkyl-1,3-propanediols utilizing a chiral sulfonamide-Zn complex catalyst

Org Lett. 2007 Feb 1;9(3):509-12. doi: 10.1021/ol063063g.

Abstract

[structure: see text] Treatment of a chiral sulfonamide with Et(2)Zn gave quantitatively its Zn complex and then the structure was determined by X-ray crystallographic analysis. Reaction of prochiral N-Boc-2-amino-2-alkyl-1,3-propanediols with Ac(2)O in the presence of 5 mol % of chiral sulfonamide-Zn complex catalyst afforded the corresponding chiral monoacetyl products in 70-92% yields with 70-88% ee values. The proposed mechanism for the catalytic monoacetylation of a prochiral 1,3-propanediol was presented on the basis of CSI-MS analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Alkylation
  • Amines / chemistry*
  • Catalysis
  • Models, Chemical
  • Models, Molecular
  • Organometallic Compounds / chemistry*
  • Propylene Glycols / chemical synthesis*
  • Stereoisomerism
  • Sulfonamides / chemistry*
  • Zinc / chemistry*

Substances

  • Amines
  • Organometallic Compounds
  • Propylene Glycols
  • Sulfonamides
  • Zinc