(S)-α-(R)-phenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol

• 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)-α-(R)-phenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol
• 英文别名: (R)-phenyl ((S)-1-tosylpyrrolidin-2-yl) methanol；(R)-phenyl((S)-N-tosylpyrrolidin-2-yl)methanol；(R)-[(2S)-1-(4-methylphenyl)sulfonylpyrrolidin-2-yl]-phenylmethanol
• 化学式: C₁₈H₂₁NO₃S
• 分子量: 331.436
• InChiKey: GIKOWNDCULNALO-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-α-(R)-phenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol 在 lithium aluminium tetrahydride 、 碳酸氢钠 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 12.67h， 生成 (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol
  参考文献：
  名称：

  Highly Stereoselective Syntheses of Proline-Derived Vicinal Amino Alcohols through Grignard Addition onto N-Tosylprolinal

  摘要：

  A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

  DOI：

  10.1055/s-0035-1560802
• 作为产物：
  描述：

  1-(甲苯-4-磺酰基)-吡咯烷-2-羧酸 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 (S)-α-(R)-phenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol
  参考文献：
  名称：

  通过超亲电活化获得光学纯净的苯乙磺胺。

  摘要：

  通过超强酸活化，源自易于获得的麻黄碱或氨基酸的N-（芳烃磺酰基）-氨基醇会经历分子内Friedel-Crafts反应，以高产率得到对映体纯的苯并阿苏二胺，并具有完全受控的非对映选择性，并带有两个相邻的立体中心。低温NMR光谱表明，构象受限的手性双效中间体具有重要作用。

  DOI：

  10.1021/acs.orglett.0c01301

文献信息

• Hemiaminals as substrates for sulfur ylides: Direct asymmetric syntheses of functionalised pyrrolidines and piperidines
  作者：Christoforos G. Kokotos、Varinder K. Aggarwal

  DOI：10.1039/b602226j

  日期：——

  Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enantioselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.

  苯基稳定手性硫叶立德与五元环半缩胺反应，可直接高对映选择性地合成功能化吡咯烷。通过分离中间环氧化物并用TMSOTf处理，该反应可转化为生成哌啶。
• Access to Optically Pure Benzosultams by Superelectrophilic Activation
  作者：Bastien Michelet、Ugo Castelli、Emeline Appert、Maude Boucher、Kassandra Vitse、Jérôme Marrot、Jérôme Guillard、Agnès Martin-Mingot、Sébastien Thibaudeau

  DOI：10.1021/acs.orglett.0c01301

  日期：2020.7.2

  N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel–Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereocenters in high yields with fully controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally restricted chiral dicationic intermediates.

  通过超强酸活化，源自易于获得的麻黄碱或氨基酸的N-（芳烃磺酰基）-氨基醇会经历分子内Friedel-Crafts反应，以高产率得到对映体纯的苯并阿苏二胺，并具有完全受控的非对映选择性，并带有两个相邻的立体中心。低温NMR光谱表明，构象受限的手性双效中间体具有重要作用。
• Highly Stereoselective Syntheses of Proline-Derived Vicinal Amino Alcohols through Grignard Addition onto N-Tosylprolinal
  作者：Alakesh Bisai、Saikat Chaudhuri、Amarchand Parida、Santanu Ghosh

  DOI：10.1055/s-0035-1560802

  日期：——

  A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.