F-AP₁₅ lipase

• 英文名称: F-AP₁₅ lipase

反应信息

• 作为试剂：
  描述：

  亚磷酸氢二甲酯 、 乙酰氯 、 丁烯-2-醛 在 titanium(IV) isopropylate 、 4(1S,2S)-trans-1,2-cyclohexanediol 、 poly(4-vinyl)pyridine 、 F-AP₁₅ lipase 作用下， 以 乙醚 、 乙腈 、 phosphate buffer 为溶剂， 以79%的产率得到(R)-dimethyl (1-acetoxy-2E-butenyl) phosphonate
  参考文献：
  名称：

  The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: titanium alkoxide-catalyzed PC bond formation and kinetic resolution

  摘要：

  Titanium alkoxide-catalyzed asymmetric phosphonylation of aldehydes yields hydroxy phosphonates in moderate to good enantiomeric excess (e.e.s similar to 70%). The hydroxy phosphonates were acetylated and the acetates were subjected to enzyme-catalyzed kinetic resolution. The non-racemic acetates 2 (predominantly (R)-enantiomer) were hydrolyzed with an (R)-enantiomer-selective lipase, resulting predominantly in the hydrolysis of the (R)-isomer (at 85% conversion) to give the alcohols 3 with high e.e. Alternatively, hydrolysis of the minor enantiomeric (S)-acetate to approximately 20% conversion left the enriched (R)-configured acetate with improved e.e. (> 90%). The moderate enantio selectivities obtained in the catalytic P-C bond formation are enhanced during the enzymatic hydrolysis. Furthermore, availability of the non-racemic phosphonates permits the use of less selective enzymes, resulting in higher yields in comparison with the standard resolution of racemic materials. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00303-2