(S)-1-{(2S,3R)-3-[(S)-1-(Diphenyl-phosphinoyl)-2-methyl-propyl]-oxiranyl}-ethanol | 145653-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-{(2S,3R)-3-[(S)-1-(Diphenyl-phosphinoyl)-2-methyl-propyl]-oxiranyl}-ethanol
• CAS: 145653-25-4
• 化学式: C₂₀H₂₅O₃P
• 分子量: 344.39
• InChiKey: UHLDTOCVCQFSFK-QLIIJSOBSA-N

反应信息

• 作为反应物：
  描述：

  (S)-1-{(2S,3R)-3-[(S)-1-(Diphenyl-phosphinoyl)-2-methyl-propyl]-oxiranyl}-ethanol 在 氢氧化钾 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 (4S,5S)-(Z)-3-Benzyl-4-(3'-methylbut-1'-enyl)-5-methyloxazolidin-2-one
  参考文献：
  名称：

  Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

  摘要：

  Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 of diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

  DOI：

  10.1016/s0040-4039(00)60383-0
• 作为产物：
  描述：

  (2RS,5RS;E)-5-diphenylphosphinoyl-6-methylhept-3-en-2-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 (E)-(2R,5R)-5-(Diphenyl-phosphinoyl)-6-methyl-hept-3-en-2-ol 、 (R)-1-{(2R,3S)-3-[(R)-1-(Diphenyl-phosphinoyl)-2-methyl-propyl]-oxiranyl}-ethanol 、 (S)-1-{(2S,3R)-3-[(S)-1-(Diphenyl-phosphinoyl)-2-methyl-propyl]-oxiranyl}-ethanol
  参考文献：
  名称：

  Asymmetric epoxidations and kinetic resolutions of δ-hydroxy allylic phosphine oxides

  摘要：

  Delta-Hydroxy allylic phosphine oxides 5 undergo asymmetric epoxidation to yield epoxy alcohols 6 with high enantio- and diastereoselectivity. Kinetic resolutions are also successful, even with a chiral centre remote from the allylic hydroxyl, if that chiral centre bears a diphenylphosphinoyl group. The diphenylphosphinoyl group then exerts a novel anti-directing effect on the epoxidation.

  DOI：

  10.1016/s0040-4039(00)60928-0