A chiral ligand-mediated asymmetric addition of a lithium BHA ester enolate to an aldehyde

Chem Pharm Bull (Tokyo). 2002 Aug;50(8):1131-4. doi: 10.1248/cpb.50.1131.

Abstract

The asymmetric reaction of a lithium enolate generated from a BHA (2, 6-di-tert-buty-4-methoxyphenyl) propanoate was allowed to react with benzaldehyde in the presence of a diether-type chiral ligand affording the corresponding anti-aldol product in a moderate enantioselectivity. A tetradentate ligand induced better enantioselectivity albeit relative loss of anti-selectivity. A variation of lithiating amide agent affected the selectivity, indicating involvement of an amine as a component of the mixed aggregate. Absolute configuration of some of the aldol products was determined by standard transformations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Butylated Hydroxyanisole / analogs & derivatives*
  • Butylated Hydroxyanisole / chemistry
  • Esters
  • Ligands
  • Lithium Compounds / chemistry*
  • Molecular Conformation

Substances

  • Aldehydes
  • Esters
  • Ligands
  • Lithium Compounds
  • Butylated Hydroxyanisole