trimethyl (2R,3S,4R,5S)-5-(4-methylphenyl)pyrrolidine-2,3,4-tricarboxylate

• 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 (2R,3S,4R,5S)-5-(4-methylphenyl)pyrrolidine-2,3,4-tricarboxylate
• 英文别名: trimethyl (2R,3S,4R,5S)-5-(p-tolyl)pyrrolidine-2,3,4-tricarboxylate；(2R,3S,4R,5S)-2,3,4-tricarbomethoxy-5-(4-methylphenyl)pyrrolidine；(2R,3S,4R,5S)-trimethyl 5-p-tolylpyrrolidine-2,3,4-tricarboxylate；trimethyl (2R,3S,4R,5S)-5-p-tolylpyrrolidine-2,3,4-tricarboxylate
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: BQJJKRKCAINNNS-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  马来酸二甲酯 、 (E)-[(4-methyl-benzylidene)-amino]-acetic acid methyl ester 在 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 C₂₈H₂₇Br₂F₁₂N₂P 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以97%的产率得到trimethyl (2R,3S,4R,5S)-5-(4-methylphenyl)pyrrolidine-2,3,4-tricarboxylate
  参考文献：
  名称：

  铜 (I)/TF-BiphamPhos 配合物催化的 Azomethine Ylides 的高对映选择性 1,3-偶极环加成反应

  摘要：

  一种新型高效的 Cu(I)/TF-BiphamPhos 催化体系在具有 0.1-3 mol% 催化剂负载的偶氮甲碱叶立德的不对称 1,3-偶极环加成反应中表现出优异的反应性、对映/非对映选择性和结构范围。本方法是偶氮甲碱叶立德不对称环加成的最佳结果，特别是在反应性和对映选择性方面，来自甘氨酸以外的氨基酯。

  DOI：

  10.1021/ja807669q

文献信息

• Asymmetric [3+2] Cycloaddition of Azomethine Ylides Catalyzed by Silver(I) Triflate with a Chiral Bipyrrolidine-Derived Phosphine Ligand
  作者：Zhen-Jiang Xu、Chi-Ming Che、Xin Gu、Vanessa Lo

  DOI：10.1055/s-0032-1316779

  日期：——

  bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized. The ‘AgOTf + L1’ protocol catalyzes the asymmetric [3+2] cycloaddition of azomethine ylides with alkenes to give highly substituted pyrrolidines in good yields (up to 90%) with moderate to high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 76%). Two novel chiral bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized

  摘要 合成了两个新颖的手性联吡咯烷衍生的膦配体L1和L2。“ AgOTf + L1 ”方案可催化偶氮甲亚胺与烯烃的不对称[3 + 2]环加成反应，以高收率（高达90％），中等至高非对映选择性（高达> 19：1 dr）提供高度取代的吡咯烷。对映选择性（高达76％）。 合成了两个新颖的手性联吡咯烷衍生的膦配体L1和L2。“ AgOTf + L1 ”方案可催化偶氮甲亚胺与烯烃的不对称[3 + 2]环加成反应，以高收率（高达90％），中等至高非对映选择性（高达> 19：1 dr）提供高度取代的吡咯烷。对映选择性（高达76％）。
• Highly Enantioselective Ag(I)-Catalyzed [3 + 2] Cycloaddition of Azomethine Ylides
  作者：James M. Longmire、Bin Wang、Xumu Zhang

  DOI：10.1021/ja025969x

  日期：2002.11.1

  A highly reactive Ag(I)-catalyzed [3 + 2] cycloaddition of azomethine ylides is founded using AgOAc as the catalytic precursor and phosphines as ligands. Using a new bis-ferrocenyl amide phosphine (FAP) as the ligand, we found that high enantioselectivities (up to 97% ee) have been achieved in the [3 + 2] cycloaddition of azomethine ylides. Up to four stereogenic centers can be established in this

  使用 AgOAc 作为催化前体和膦作为配体，建立了高活性 Ag(I) 催化的 [3 + 2] 环加成反应。使用新的双二茂铁基酰胺膦 (FAP) 作为配体，我们发现在偶氮甲碱叶立德的 [3 + 2] 环加成反应中实现了高对映选择性（高达 97% ee）。在这种多组分偶联反应中，可以从容易获得的材料（如醛、氨基酯和亲偶极体）建立多达四个立体中心。
• New chiral ferrocenyl P,S-ligands for highly diastereo- and enantioselective Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
  作者：Mei-Ling Han、Dao-Yong Wang、Pei-Wei Zeng、Zhuo Zheng、Xiang-Ping Hu

  DOI：10.1016/j.tetasy.2012.02.017

  日期：2012.2

  A new family of chiral ferrocenyl P,S-ligands incorporating an indole ring at the alpha-ferrocenylmethyl position has been prepared via a Friedel-Crafts alkylation reaction of (R-c,S-Fc)-PPFA with a variety of 2-indole thioethers. These newly developed ferrocenyl P,S-ligands proved to be efficient in the AgOAc-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with various dipolarophiles, giving cycloadducts with high diastereoselectivities and enantioselectivities (up to 99% ee). (C) 2012 Elsevier Ltd. All rights reserved.
• Enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides using a chiral ferrocene-based phosphine–phosphoramidite ligand having a stereogenic P-center
  作者：Sai-Bo Yu、Xiang-Ping Hu、Jun Deng、Dao-Yong Wang、Zheng-Chao Duan、Zhuo Zheng

  DOI：10.1016/j.tetasy.2009.02.058

  日期：2009.3

  A series of chiral ferrocene-based phosphine-phosphoramidite ligands (PPFAPhos) have been employed in the Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with dimethyl maleate. The results showed that the ligand with a stereogenic P-center in the phosphino moiety displayed the best diastereo- and enantioselectivities, in which LIP to 99% enantiomeric excesses and 99/1 endo/exo selectivities have been achieved. (C) 2009 Elsevier Ltd. All rights reserved.
• Highly Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides Catalyzed by Copper(I)/TF-BiphamPhos Complexes
  作者：Chun-Jiang Wang、Gang Liang、Zhi-Yong Xue、Feng Gao

  DOI：10.1021/ja807669q

  日期：2008.12.24

  A new and highly efficient Cu(I)/TF-BiphamPhos catalytic system exhibited excellent reactivity, enantio-/diastereoselectivity, and structural scope in asymmetric 1,3-dipolar cycloaddition of azomethine ylides with 0.1-3 mol % of catalyst loading. The present methodology is the best result for asymmetric cycloaddition of azomethine ylides, especially derived from amino esters other than glycinate in

  一种新型高效的 Cu(I)/TF-BiphamPhos 催化体系在具有 0.1-3 mol% 催化剂负载的偶氮甲碱叶立德的不对称 1,3-偶极环加成反应中表现出优异的反应性、对映/非对映选择性和结构范围。本方法是偶氮甲碱叶立德不对称环加成的最佳结果，特别是在反应性和对映选择性方面，来自甘氨酸以外的氨基酯。