Abstract
Stereoselective oxidative coupling of carboxylic acid derivatives and reductive coupling of cinnamic acid derivatives using chiral auxiliaries are described as the following items. 1) Oxidative homocoupling of chiral 3- (arylacetyl)-2-oxazolidinones with DABCO-TiCl4 or DMAP-TiCl4. 2) Oxidative homocoupling of (4S)-3-(3-arylpropanoyl)-4-isopropyl-2-oxazolidinones and (4R, 5S)-1-(3-arylpropanoyl)-3, 4-dimethyl-5-phenyl-2-imidazolidinones with LDA as a base and TiCl4, PhI (OAc)2, or CuCl2 as an oxidant. 3) Oxidative coupling of (4R, 5S)-1-aroylacetyl-3, 4-dimethyl-5-phenyl-2-imidazolidinones with NaH-Br2 and oxidative intramolecular coupling of diaroylacetate derivatives prepared from (1R, 1'R)-exo, exo'-3, 3'-biisoborneol with NaH-Br2. 4) Electroreductive hydrocoupling of chiral 3-cinnamoyl-2-oxazolidinones and cinnamates of [(1R)-exo]-3-exo-(diphenylmethyl) borneol. 5) Electroreductive cross-coupling of chiral 3-cinnamoyl-2-oxazolidinones with acid anhydrides.
