benzyl-tert-butylmethylphosphane-borane | 263768-81-6

• 英文名称: benzyl-tert-butylmethylphosphane-borane
• 英文别名: benzyl-t-butylmethylphosphine-borane
• CAS: 263768-81-6
• 化学式: C₁₂H₂₂BP
• 分子量: 208.091
• InChiKey: IVMSOSXIYBLDCA-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  氯化苄 、 t-butylmethylphenylphosphine borane 在 氨 、 氢化钾 、 氯代叔丁烷 作用下， 反应 1.5h， 以54%的产率得到benzyl-tert-butylmethylphosphane-borane
  参考文献：
  名称：

  芳基膦衍生物的原位脱芳构化/烷基化

  摘要：

  芳基二烷基膦-硼烷和芳基二烷基膦氧化物在 Birch 还原条件下脱芳构化，然后用反应性烷基卤化物处理，提供相应的 α-官能化（环六-1,4-二烯-3-基）膦衍生物。该反应为合成大体积（环己二烯基）膦提供了一种选择方法。

  DOI：

  10.1002/ejoc.201200096

文献信息

• Kinetic resolution of P-stereogenic phosphine boranes via deprotonation using s-butyllithium/(−)-sparteine
  作者：Johan Granander、Francesco Secci、Peter O’Brien、Brian Kelly

  DOI：10.1016/j.tetasy.2009.10.026

  日期：2009.11

  The attempted kinetic resolution of racemic secondary phosphine boranes [t-BuPhP(BH3)H and t-BuMeP(BH3)H] by P-H deprotonation using 0.5 equiv of s-BuLi and (-)-sparteine was unsuccessful and generated racemic benzyl bromide-trapped adducts in 42-49% yield. In contrast, an efficient kinetic resolution was observed with racemic tertiary phosphine boranes [t-BuPhP(BH3)Me and t-BuEtP(BH3)Me] by C-H deprotonation on the P-Me group using 0.5 or 0.6 equiv of s-BuLi and (-)-sparteine. For example, the use of 0.6 equiv of s-BuLi/(-)-sparteine with t-BuEtP(BH3)Me and trapping with DMF gave the (R)-aldehyde adduct in 37% yield and 83:17 er together with recovered (R)-t-BuEtP(BH3)Me in 44% yield and 74:26 er. These are the first examples of kinetic resolution of P-stereogenic phosphine boranes via deprotonation using s-BuLi/(-)-sparteine. (C) 2009 Elsevier Ltd. All rights reserved.