(S)-3-allyl-1,3-dimethylindolin-2-one | 886225-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-3-allyl-1,3-dimethylindolin-2-one
• 英文别名: (3S)-1,3-dimethyl-3-prop-2-enylindol-2-one
• CAS: 886225-86-1
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: ABUYRUJFTIHWJO-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (±)-allyl 2-methyl-3-(methyl(phenyl)amino)-3-oxopropanoate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 (R,R)-ANDEN-phenyl Trost ligand 、 copper(II) acetate monohydrate 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 39.0h， 生成 (S)-3-allyl-1,3-dimethylindolin-2-one 、 (R)-3-allyl-1,3-dimethylindolin-2-one
  参考文献：
  名称：

  Asymmetric Decarboxylative Allylation of Oxindoles

  摘要：

  An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.

  DOI：

  10.1021/ol201613a

文献信息

• Molybdenum-Catalyzed Asymmetric Allylic Alkylation of 3-Alkyloxindoles: Reaction Development and Applications
  作者：Barry M. Trost、Yong Zhang

  DOI：10.1002/chem.201002569

  日期：2011.3.1

  the development of Mo‐catalyzed asymmetric allylic alkylation reactions with 3‐alkyloxindoles as nucleophiles. The reaction is complementary to the Pd‐catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3‐alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good‐to‐excellent enantioselectivities. Applications of this

  我们报告了我们在开发以 3-烷基羟吲哚作为亲核试剂的 Mo 催化的不对称烯丙基烷基化反应方面所做的工作。就羟吲哚亲核试剂的范围而言，该反应与 Pd 催化反应互补。许多3-烷基羟吲哚在温和条件下成功烷基化，得到具有优异收率和良好对映选择性的产品。据报道，该方法应用于制备二氢吲哚生物碱，如 (-)-毒扁豆碱、ent- (-)-去溴氟曲明 B 和 communesin B 的吲哚啉喹啉环。
• <i>C</i> ₂-Symmetric atropisomeric N-heterocyclic carbene–palladium(<scp>ii</scp>) complexes: synthesis, chiral resolution, and application in the enantioselective α-arylation of amides
  作者：Lingyu Kong、Yajie Chou、Muriel Albalat、Marion Jean、Nicolas Vanthuyne、Stéphane Humbel、Paola Nava、Hervé Clavier

  DOI：10.1039/d3dt01182h

  日期：——

  The concept of atropisomeric N-heterocyclic carbene (NHC)–metal complexes was extended to NHCs possessing a C2-symmetry and implemented to prepare palladium-based complexes. An in-depth study of the NHC precursors and the screening of various NHC ligands enabled us to circumvent the issue associated with the formation of meso complexes. A set of 8 atropisomeric NHC–palladium complexes were prepared

  阻转异构N-杂环卡宾(NHC)-金属配合物的概念被扩展到具有C 2对称性的NHC，并用于制备钯基配合物。对 NHC 前体的深入研究和各种 NHC 配体的筛选使我们能够规避与内消旋复合物形成相关的问题。制备了一组 8 种阻转异构体 NHC-钯配合物，并通过手性 HPLC 在制备规模上进行有效拆分，获得了高对映体纯度。这些配合物在酰胺的分子内 α-芳基化中表现出良好的活性，并且以优异的对映选择性（高达 98% ee）分离出各种环状产物。
• Asymmetric Decarboxylative Allylation of Oxindoles
  作者：Vilius Franckevičius、James D. Cuthbertson、Mark Pickworth、David S. Pugh、Richard J. K. Taylor

  DOI：10.1021/ol201613a

  日期：2011.8.19

  An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.