Acyclic amino acid-catalyzed direct asymmetric aldol reactions: alanine, the simplest stereoselective organocatalyst

Chem Commun (Camb). 2005 Jul 28:(28):3586-8. doi: 10.1039/b507968n. Epub 2005 Jun 21.

Abstract

The linear amino acid-catalyzed direct asymmetric intermolecular aldol reaction is presented; simple amino acids such as alanine, valine, isoleucine, aspartate, alanine tetrazole and serine catalyzed the direct catalytic asymmetric intermolecular aldol reactions between unmodified ketones and aldehydes with excellent stereocontrol and furnished the corresponding aldol products in up to 98% yield and with up to > 99% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / chemistry*
  • Alcohols
  • Aldehydes
  • Amino Acids / chemistry*
  • Catalysis*
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Amino Acids
  • Alanine