A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst

Org Biomol Chem. 2012 Aug 7;10(29):5613-9. doi: 10.1039/c2ob25693b. Epub 2012 Jun 20.

Abstract

A tripeptide-like prolinamide-thiourea catalyst with (S)-proline, (1S,2S)-diphenylethylenediamine and (S)-di-tert-butyl aspartate as building blocks provides the products of the reaction between ketones and aromatic aldehydes in high to quantitative yields and high stereoselectivities (up to 99:1 dr and 99% ee). Both the chiral centers of the diamine unit are essential, while the thiourea hydrogen originating from the amine and the amide hydrogen play a predominant role for the catalyst efficiency.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Catalysis
  • Ethylenediamines / chemistry
  • Hydrogen / chemistry
  • Isomerism
  • Ketones / chemistry
  • Oligopeptides / chemistry*
  • Proline / analogs & derivatives*
  • Proline / chemistry
  • Stereoisomerism
  • Thiourea / chemistry*

Substances

  • Aldehydes
  • Ethylenediamines
  • Ketones
  • Oligopeptides
  • diphenylethylenediamine
  • Hydrogen
  • Proline
  • Thiourea
  • prolinamide