trimethyl (2S,3S,4R,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate | 479499-36-0

• 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,3S,4R,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate
• CAS: 479499-36-0
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: GIFDWMSXDIZYQF-VOAKCMCISA-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

• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 tetrakis(acetonitrile)copper(I) perchlorate 、 magnesium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 trimethyl (2S,3S,4R,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate
  参考文献：
  名称：

  CuI–Fesulphos complexes: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides

  摘要：

  The Cu-I-Fesulphos catalyst system (<= 3 mol %) shows an excellent performance in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. High to very high levels of reactivity, endo/exo selectivity, and enantioselectivity ( 69->99% ee) are generally achieved with a very wide range of azomethine ylides and dipolarophiles. Based on experimental and computational studies data, a model that accounts for this high enantiocontrol is proposed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.130

文献信息

• Highly Enantioselective Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylide Catalyzed by a Copper(I)/ClickFerrophos Complex
  作者：Shin-ichi Fukuzawa、Hiroshi Oki

  DOI：10.1021/ol8003996

  日期：2008.5.1

  A copper(I)/ClickFerrophos complex catalyzed the asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with vinyl sulfone to give the exo-2,4,5-trisubstituted pyrrolidine in good yield with high enantioselectivity (99% ee). The complex also effectively catalyzed reactions of other dipolarophiles such as acrylates, maleate, and maleimides to

  铜（I）/ ClickFerrophos络合物催化N-亚苄基甘氨酸甲酯（偶氮甲亚胺基化物的来源）与乙烯基砜的不对称1,3-偶极环加成反应，以高收率得到exo-2,4,5-三取代的吡咯烷，高对映选择性（99％ee）。该配合物还有效地催化其他双亲性试剂如丙烯酸酯，马来酸酯和马来酰亚胺的反应，得到具有高非对映和对映选择性的exo-2,4,5-和2,3,4,5-取代的吡咯烷衍生物。
• 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％）。
• Cu II -catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with a chiral ferrocene-derived P,N-ligand
  作者：Bilel Bdiri、Li Dai、Zhi-Ming Zhou

  DOI：10.1016/j.tetlet.2017.05.044

  日期：2017.6

  A ferrocene-derived P,N-heterodonor ligand was effectively used in a Cu(OAc)2·H2O-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with maleate derivatives, affording cycloadducts with high yields (up to 96%), diastereoselectivities (>99 dr), and enantioselectivities (up to 99% ee).

  二茂铁衍生的P，N-异杂炔配体可有效地用于Cu（OAc）2 ·H 2 O催化的偶氮甲亚胺与马来酸酯衍生物的不对称1,3-偶极环加成反应，提供高收率的环加合物（高达96％ ），非对映选择性（> 99 dr）和对映选择性（最高99％ee）。
• CuI–Fesulphos complexes: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides
  作者：Silvia Cabrera、Ramón Gómez Arrayás、Belén Martín-Matute、Fernando P. Cossío、Juan C. Carretero

  DOI：10.1016/j.tet.2007.03.130

  日期：2007.7

  The Cu-I-Fesulphos catalyst system (<= 3 mol %) shows an excellent performance in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. High to very high levels of reactivity, endo/exo selectivity, and enantioselectivity ( 69->99% ee) are generally achieved with a very wide range of azomethine ylides and dipolarophiles. Based on experimental and computational studies data, a model that accounts for this high enantiocontrol is proposed. (c) 2007 Elsevier Ltd. All rights reserved.