2,2-Dimethyl-propionic acid (E)-(S)-5-hydroxy-7-phenyl-hept-6-enyl ester | 180923-20-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 2,2-Dimethyl-propionic acid (E)-(S)-5-hydroxy-7-phenyl-hept-6-enyl ester
• CAS: 180923-20-0
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: XXBDGYVVDFSDIG-DBTPVHCXSA-N

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (E)-(S)-5-hydroxy-7-phenyl-hept-6-enyl ester 在 三乙烯二胺 、 咪唑 、 potassium dioxotetrahydroxoosmate(VI) 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 40.0h， 生成 2,2-Dimethyl-propionic acid (S)-6,7-dihydroxy-7-phenyl-5-triisopropylsilanyloxy-heptyl ester
  参考文献：
  名称：

  Catalytic asymmetric synthesis of protected α-hydroxy aldehydes and related 1,2-difunctional chiral building blocks. An enantioselective synthesis of (−)-exo- and (−)-endo-brevicomin

  摘要：

  Chiral allylic alcohols which were prepared by the addition of functionalized dialkylzincs to alpha,beta-unsaturated aldehydes in good to excellent enantioselectivity, were converted to protected alpha-hydroxy aldehydes and 1,2-amino alcohols without loss of enantiomeric purity. Syn- or anti-1,2-diols can be obtained stereoselectively by a second asymmetric addition to alpha-silyloxy aldehydes. Functionalized 1,2-diols prepared in this way were converted to enantiomerically pure (-)-exo- and (-)-endo-brevicomin (>99% ee). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00036-0
• 作为产物：
  描述：

  反式肉桂醛 、 di(4-pivaloyloxybutyl)zinc 在 titanium(IV) isopropylate 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 作用下， 生成 2,2-Dimethyl-propionic acid (E)-(S)-5-hydroxy-7-phenyl-hept-6-enyl ester 、 2,2-Dimethyl-propionic acid (E)-(R)-5-hydroxy-7-phenyl-hept-6-enyl ester
  参考文献：
  名称：

  Catalytic asymmetric synthesis of protected α-hydroxy aldehydes and related 1,2-difunctional chiral building blocks. An enantioselective synthesis of (−)-exo- and (−)-endo-brevicomin

  摘要：

  Chiral allylic alcohols which were prepared by the addition of functionalized dialkylzincs to alpha,beta-unsaturated aldehydes in good to excellent enantioselectivity, were converted to protected alpha-hydroxy aldehydes and 1,2-amino alcohols without loss of enantiomeric purity. Syn- or anti-1,2-diols can be obtained stereoselectively by a second asymmetric addition to alpha-silyloxy aldehydes. Functionalized 1,2-diols prepared in this way were converted to enantiomerically pure (-)-exo- and (-)-endo-brevicomin (>99% ee). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00036-0