N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: a practical proline mimetic for facilitating enantioselective aldol reactions

Org Lett. 2008 Oct 16;10(20):4649-52. doi: 10.1021/ol801941j. Epub 2008 Sep 23.

Abstract

A highly practical and readily available proline surrogate has been developed with improved solubility properties in common, nonpolar organic solvents. This sulfonamide-based catalyst has proven highly effective at facilitating enantioselective and diastereoselective aldol reactions with a range of substrates in nonpolar organic solvents in the presence of a single equivalent of water. Additionally, catalyst loading as low as 2 mol % can be employed in the absence of any organic solvent with continued high levels of selectivity.

Publication types

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

MeSH terms

  • Aldehydes / chemistry*
  • Biomimetic Materials / chemistry*
  • Catalysis
  • Molecular Structure
  • Proline / chemistry
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Stereoisomerism
  • Sulfonamides / chemistry
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry

Substances

  • Aldehydes
  • N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide
  • Pyrrolidines
  • Sulfonamides
  • Sulfones
  • 3-hydroxybutanal
  • Proline