不斉補助基を用いた立体選択的な酸化・還元カップリング
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概要
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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-TiCl<SUB>4</SUB> or DMAP-TiCl<SUB>4</SUB>. 2) Oxidative homocoupling of (4<I>S</I>)-3-(3-arylpropanoyl)-4-isopropyl-2-oxazolidinones and (4<I>R</I>, 5<I>S</I>)-1-(3-arylpropanoyl)-3, 4-dimethyl-5-phenyl-2-imidazolidinones with LDA as a base and TiCl<SUB>4</SUB>, PhI (OAc)<SUB>2</SUB>, or CuCl<SUB>2</SUB> as an oxidant. 3) Oxidative coupling of (4<I>R</I>, 5<I>S</I>)-1-aroylacetyl-3, 4-dimethyl-5-phenyl-2-imidazolidinones with NaH-Br<SUB>2</SUB> and oxidative intramolecular coupling of diaroylacetate derivatives prepared from (1<I>R</I>, 1<I>R</I>)-<I>exo, exo</I>-3, 3-biisoborneol with NaH-Br<SUB>2</SUB>. 4) Electroreductive hydrocoupling of chiral 3-cinnamoyl-2-oxazolidinones and cinnamates of [(1<I>R</I>)-<I>exo</I>]-3-<I>exo</I>-(diphenylmethyl) borneol. 5) Electroreductive cross-coupling of chiral 3-cinnamoyl-2-oxazolidinones with acid anhydrides.
- 社団法人 有機合成化学協会の論文
- 2004-04-01