Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions

Org Biomol Chem. 2010 Sep 21;8(18):4085-9. doi: 10.1039/c0ob00049c. Epub 2010 Jul 12.

Abstract

A pyridine based 1,2-diamine containing only one stereogenic center has been identified for fast aldol reactions (16-48 h). Using 2-5 mol% of (R)- or (S)-PicAm-2, cyclohexanone (3.3 equiv) readily undergoes aldol reactions with o-, m-, and p-substituted aromatic aldehyde partners (limiting reagent), including the poor electrophile 4-methylbenzaldehyde (95-99% ee). Furthermore, functionalized cyclic ketone substrates have been converted into four aldol products 9-12 using the lowest catalyst loading (5.0 mol%) to date with the highest yield and enantioselectivity.

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Aldehydes / chemistry*
  • Catalysis
  • Diamines / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Picolines / chemistry*
  • Stereoisomerism
  • Water / chemistry

Substances

  • Alcohols
  • Aldehydes
  • Diamines
  • Ketones
  • Picolines
  • Water