Increased structural complexity leads to higher activity: peptides as efficient and versatile catalysts for asymmetric aldol reactions

Org Lett. 2005 Mar 17;7(6):1101-3. doi: 10.1021/ol0500259.

Abstract

[reaction: see text] Peptides containing a secondary amine and a carboxylic acid in a specific orientation to each other are presented as highly efficient catalysts for asymmetric aldol reactions: (1) their activity is considerably higher compared to that of proline, and (2) the enantioselectivity of the peptidic catalysts can be changed from (R)- to (S)-selectivity by simple modifications of the secondary structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Molecular Structure
  • Peptides / chemistry*
  • Proline / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Aldehydes
  • Amines
  • Peptides
  • 3-hydroxybutanal
  • Proline