(2S)-1-diphenylphosphinothioylpyrrolidine-2-carboxylic acid | 61057-98-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-1-diphenylphosphinothioylpyrrolidine-2-carboxylic acid
• CAS: 61057-98-5
• 化学式: C₁₇H₁₈NO₂PS
• 分子量: 331.375
• InChiKey: GOPFNGSZQBXDKT-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-1-diphenylphosphinothioylpyrrolidine-2-carboxylic acid 在 4-二甲氨基吡啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Two-fold amino acid-based chiral aminophosphine–oxazolines and use in asymmetric allylic alkylation

  摘要：

  Chiral aminophosphine-oxazoline ligands derived from two different amino acids (tetrahydroisoquinoline carboxylic acid and proline) have been synthesized and examined as chiral auxiliaries in asymmetric allylic alkylation of three substrates. Stereoisomers la and 2a are providing the highest enantio selectivities (up to 94% ee) in the allylation of diphenylpropenyl acetate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01561-2
• 作为产物：
  描述：

  L-脯氨酸甲酯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 37.0h， 生成 (2S)-1-diphenylphosphinothioylpyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Two-fold amino acid-based chiral aminophosphine–oxazolines and use in asymmetric allylic alkylation

  摘要：

  Chiral aminophosphine-oxazoline ligands derived from two different amino acids (tetrahydroisoquinoline carboxylic acid and proline) have been synthesized and examined as chiral auxiliaries in asymmetric allylic alkylation of three substrates. Stereoisomers la and 2a are providing the highest enantio selectivities (up to 94% ee) in the allylation of diphenylpropenyl acetate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01561-2

文献信息

• Asymmetric hydrogenation of aromatic olefins catalyzed by iridium complexes of proline derived phosphine–oxazoline ligands
  作者：Guopin Xu、Scott R. Gilbertson

  DOI：10.1016/s0040-4039(02)02747-8

  日期：2003.1

  phosphine–oxazoline ligands is reported. This ligands are synthesized by reaction of a phosphine chloride with the secondary nitrogen of proline. Upon coordination to iridium the resulting complexes can be used in the asymmetric hydrogenation of simple olefins. The effect of different counter ions and substitution at the oxazoline and the phosphine is reported.

  报道了一系列膦-恶唑啉配体的合成。该配体通过氯化膦与脯氨酸的仲氮反应合成。与铱配位后，所得络合物可用于简单烯烃的不对称氢化。报道了不同的​​抗衡离子和在恶唑啉和膦处的取代作用。
• Facile synthesis of proline based phosphineoxazoline ligands by formation of a PN bond
  作者：Guopin Xu、Scott R Gilbertson

  DOI：10.1016/s0040-4039(02)00346-5

  日期：2002.4

  A series of new P-N ligands in which the phosphorus moiety is introduced by Formation of a phosphorus-heteroatom bond are synthesized. These ligands are based on proline with chiral centers from both proline and an oxazoline. The two chiral centers are responsible for the observed stereoselectivity. Palladium complexes of these ligands are shown to be effective in the allylation of dimethyl malonate as well as amination of allyl acetates. (C) 2002 Elsevier Science Ltd. All rights reserved.
• UEHKI, MASAAKI;RINEHKAVA, NORIO
  作者：UEHKI, MASAAKI、RINEHKAVA, NORIO

  DOI：——

  日期：——
• UEHKI, MASAAKI;IKEHDA, SIGEHRU
  作者：UEHKI, MASAAKI、IKEHDA, SIGEHRU

  DOI：——

  日期：——
• Two-fold amino acid-based chiral aminophosphine–oxazolines and use in asymmetric allylic alkylation
  作者：Catherine Blanc、Jérôme Hannedouche、Francine Agbossou-Niedercorn

  DOI：10.1016/s0040-4039(03)01561-2

  日期：2003.8

  Chiral aminophosphine-oxazoline ligands derived from two different amino acids (tetrahydroisoquinoline carboxylic acid and proline) have been synthesized and examined as chiral auxiliaries in asymmetric allylic alkylation of three substrates. Stereoisomers la and 2a are providing the highest enantio selectivities (up to 94% ee) in the allylation of diphenylpropenyl acetate. (C) 2003 Elsevier Ltd. All rights reserved.