trimethyl (2S,3R,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate | 144538-28-3

• 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: trimethyl (2S,3R,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate
• 英文别名: (2S,3R,4S,5R)-2,3,4-tricarbomethoxy-5-phenylpyrrolidine；(2S,3R,4S,5R)-trimethyl 5-phenylpyrrolidine-2,3,4-tricarboxylate
• CAS: 144538-28-3
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: GIFDWMSXDIZYQF-RNJOBUHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trimethyl (2S,3R,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2R,3R,4S,5R)-2,3,4-tri(carbomethoxy)-5-phenylpyrrolidine
  参考文献：
  名称：

  New Zinc(II)-Based Catalyst for Asymmetric Azomethine Ylide Cycloaddition Reactions

  摘要：

  A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.

  DOI：

  10.1021/ol061521f
• 作为产物：
  描述：

  (2S,5R,6S,8R,9R)-5,6,7-triphenyl-8,9-dicarbomethoxy-1-aza-4-oxabicyclo<4.3.0>nonan-3-one 在 lead(IV) acetate 、 盐酸 作用下， 反应 6.17h， 生成 trimethyl (2S,3R,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate
  参考文献：
  名称：

  Asymmetric [1,3]-dipolar cycloaddition reactions: synthesis of highly substituted proline derivatives

  摘要：

  The asymmetric [1,3]-dipolar cycloaddition reactions of azomethine ylides derived from (5R,6S)-2,3,5,6-tetrahydro-5,6-diphenyl-1,4-oxazin-2-one with various aldehydes and dimethyl maleate is described. The reactions prove to be highly endo-selective, installing three contiguous stereogenic centers in the newly formed five-membered ring with essentially complete stereochemical control. In the case of aldehydes higher than formaldehyde, a fourth stereogenic center is created; in most cases, poor stereoselectivity is observed at this center; the diastereomers formed in these cases can be separated by chromatography and separately converted into the amino acids. The bicyclic dipolar adducts can be cleaved with either catalytic hydrogenolysis or hydrolytic ring opening, esterification, and lead tetraacetate removal of the chiral auxiliary.

  DOI：

  10.1021/jo00050a029

文献信息

• l-tert-Leucine-Derived AmidPhos–Silver(I) Chiral Complexes for the Asymmetric [3+2] Cycloaddition of Azomethine Ylides
  作者：Haifei Wang、Zhipeng Zhou、Xiaojun Zheng、Jialin Liu、Jinlei Li、Pushan Wen

  DOI：10.1055/s-0036-1588137

  日期：——

  The l -tert-leucine-derived AmidPhos/silver(I) catalytic system has been developed for the asymmetric [3+2] cycloaddition of azomethine ylides with electronic-deficient alkenes with or without Et3N. Under optimal conditions, highly functionalized endo-4-pyrrolidines were obtained with modest to high yields (up to 99% yield) and enantioselectivities (up to 98% ee).

  L-叔亮氨酸衍生的 AmidPhos/silver(I) 催化体系已开发用于在有或没有 Et3N 的情况下，偶氮甲碱叶立德与缺电子烯烃的不对称 [3+2] 环加成反应。在最佳条件下，以中等至高产率（高达 99% 的产率）和对映选择性（高达 98% ee）获得高度官能化的内 4-吡咯烷。
• Chiral 1,2-Diaminocyclohexane-α-Amino Acid-Derived Amidphos/Ag(I)-Catalyzed Divergent Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides
  作者：Jie Luo、Youshi Liu、Haifei Wang、Chuliang Gong、Zhipeng Zhou、Qingxia Zhou

  DOI：10.3987/com-21-14561

  日期：——

  1,3-dipolar cycloaddition with different electron-deficient alkenes. Among these, the (1S,2S)-1,2-cyclohexanediamine-L-tert-leucine-derived amidphos/Ag(I) has been demonstrated as being a highly efficient catalytic system in the cis-1,2-disubstituted electron-deficient olefins-involved 1,3-dipolar cycloaddition of azomethine ylides, including a series of aromatic, heteroaromatic, aliphatic, and 2-substituted

  已经开发了一系列手性 1,2-二氨基环己烷-α-氨基酸衍生的氨基膦与银 (I) 盐的组合，以协同催化偶氮甲碱叶立德与不同缺​​电子烯烃的 1,3-偶极环加成反应。其中，(1 S , 2 S )-1,2-环己二胺-L-叔-亮氨酸衍生的amidphos /Ag(I)已被证明是顺式-1,2-的高效催化体系双取代缺电子烯烃涉及偶氮甲碱叶立德的 1,3-偶极环加成，包括一系列芳族、杂芳族、脂肪族和 2-取代偶氮甲碱叶立德，以高至优异的产率提供各种完全取代的吡咯烷（产率高达 97% ) 和对映选择性（高达 97% ee）。有趣的是，(1 R , 2 R )-1,2-环己二胺-L-叔-亮氨酸衍生的酰胺磷/Ag(I)可以有效地催化末端缺电子烯烃参与的1,3-偶极环加成反应，产生一系列的 2 , 4 , 5 -三-取代的吡咯烷具有高达 92% 的产率和 92% ee。
• Bifunctional AgOAc-Catalyzed Asymmetric [3 + 2] Cycloaddition of Azomethine Ylides
  作者：Wei Zeng、Yong-Gui Zhou

  DOI：10.1021/ol0520370

  日期：2005.10.1

  [reaction: see text] A bifunctional AgOAc-catalyzed asymmetric cycloaddition of azomethine ylides with electronic-deficient alkenes was developed using ferrocenyloxazoline-derived N,P ligands. The reactive metal-bound azomethine ylide dipole is formed by the deprotonation with acetate, and extra base is not necessary. The reactions proceed with high enantioselectivity. This method provides an efficient

  [反应：见正文]使用二茂铁基恶唑啉衍生的N，P配体开发了双官能AgOAc催化的偶氮甲亚胺与电子缺陷烯烃的不对称环加成反应。通过与乙酸盐的去质子化反应，与反应性金属结合的偶氮甲碱叶立德偶极子形成，并且不需要额外的碱。反应以高对映选择性进行。该方法提供了制备旋光吡咯烷衍生物的有效且方便的途径。
• Chiral ferrocenyl P,S-ligands for highly efficient copper-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
  作者：Fu-Zhong Han、Sai-Bo Yu、Cheng Zhang、Xiang-Ping Hu

  DOI：10.1016/j.tet.2015.01.003

  日期：2016.5

  on benzimidazole and imidazole backbones have been prepared from Ugi's amine through a three-step transformation. These ligands were successfully employed in the Cu-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with various electron-deficient olefins, giving the corresponding cycloadducts in high endo-selectivities and excellent enantioselectivities (up to 99% ee).

  通过三步转化，由乌吉的胺制备了一系列基于苯并咪唑和咪唑骨架的手性二茂铁基P，S-配体。这些配体已成功地用于铜催化的偶氮甲亚胺与各种缺电子的烯烃的不对称[3 + 2]环加成中，从而以较高的内选择性和出色的对映选择性（高达99％ee）得到相应的环加合物。
• Ag₂CO₃/CA-AA-AmidPhos Multifunctional Catalysis in the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides
  作者：Haifei Wang、Qifu Deng、Zhipeng Zhou、Shunqin Hu、Zhiguo Liu、Li-Yi Zhou

  DOI：10.1021/acs.orglett.5b03430

  日期：2016.2.5

  The new Ag2CO3/CA-AA-amidphos complexes have been demonstrated as highly efficient multifunctional catalysts in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. Under optimal conditions, highly functionalized endo-4 pyrrolidines were obtained with excellent yields (up to 99% yield) and enantioselectivities (up to 96% ee).

  新的Ag 2 CO 3 / CA-AA-ami胺磷配合物已被证明是偶氮甲亚胺不对称1,3-偶极环加成反应中的高效多功能催化剂。在最佳条件下，高度官能化内切- 4克具有优异的产率（高达99％的产率）和对映选择性（高达96％ee）的得到的吡咯烷。