(R)-2-(p-bromophenyl)-1-(p-toluenesulfonyl)aziridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-(p-bromophenyl)-1-(p-toluenesulfonyl)aziridine
• 英文别名: (R)-2-(4-bromophenyl)-1-tosylaziridine；(2R)-2-(4-bromophenyl)-1-(4-methylphenyl)sulfonylaziridine
• 化学式: C₁₅H₁₄BrNO₂S
• 分子量: 352.252
• InChiKey: OGKVLFFBWMYUDN-MYJWUSKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-N-(4-溴苯亚甲基)-4-甲基苯磺酰胺 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 (R)-2-(p-bromophenyl)-1-(p-toluenesulfonyl)aziridine
  参考文献：
  名称：

  Highly stereoselective aziridination of imines with (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide

  摘要：

  Addition of (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide to N-tosyl imines afforded the corresponding sulfinyl aziridines with full enantio- and diastereoselectivity. The chiral sulfinyl substituent was removed without ring opening leading to enantiopure 2-substituted aziridines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.117

文献信息

• Design of a robust Ru(salen) complex: aziridination with improved turnover number using N-arylsulfonyl azides as precursorsElectronic supplementary information (ESI) available: typical experimental procedures, determination of enantiomeric excess and elementary analysis for complexes 3 and 5. See http://www.rsc.org/suppdata/cc/b4/b407693a/
  作者：Kazufumi Omura、Tatsuya Uchida、Ryo Irie、Tsutomu Katsuki

  DOI：10.1039/b407693a

  日期：——

  A new robust fluorinated (OC)Ru(salen) complex was designed on the basis of an X-ray structure of its parent complex to show improved turnover numbers (up to 878) and enantioselectivities (up to 99%) in aziridination reactions using p-toluenesulfonyl (Ts) or p-nitrobenzenesulfonyl (Ns) azide as the nitrene precursor; the latter is synthetically advantageous since the Ns group is N-protecting and can

  根据其母体配合物的X射线结构设计了一种新的强健的氟化（OC）Ru（salen）配合物，以显示使用p进行的叠氮化反应中改进的周转次数（至多878）和对映选择性（至多99％） -甲苯磺酰基（Ts）或对硝基苯磺酰基（Ns）叠氮化物作为腈前体；后者在合成上是有利的，因为Ns基团是N-保护的并且可以在温和的条件下被除去。
• Enantioselective Aziridination and Amination Using<i>p</i>-Toluenesulfonyl Azide in the Presence of Ru(salen)(CO) Complex
  作者：Kazufumi Omura、Masakazu Murakami、Tatsuya Uchida、Ryo Irie、Tsutomu Katsuki

  DOI：10.1246/cl.2003.354

  日期：2003.4

  (R,R)-Ru(salen)(CO) complex (1) was found to catalyze enantioselective aziridination of conjugated terminal olefins and allylic C–H amination of conjugated olefins bearing geminal- and/or trans-substituent(s) in the presence of p-toluenesulfonyl azide.

  研究发现，(R,R)-Ru(salen)(CO)配合物（1）能够在对甲苯磺酰叠氮的存在下催化共轭末端烯烃的手性选择性氮杂环丙烷化和具有双取代和/或反式取代基的共轭烯烃的烯丙位C-H胺化反应。
• Kinetic Resolution of Aziridines Enabled by N‐Heterocyclic Carbene/Copper Cooperative Catalysis: Carbene Dose‐Controlled Chemo‐Switchability
  作者：Zi‐Jing Zhang、Yu‐Hua Wen、Jin Song、Liu‐Zhu Gong

  DOI：10.1002/anie.202013679

  日期：2021.2.8

  dynamic kinetic asymmetric transformation (DyKAT) are alternative and complementary avenues to access chiral stereoisomers of both starting materials and reaction products. The development of highly efficient chiral catalytic systems for kinetically controlled processes has therefore been one of the linchpins in asymmetric synthesis. N‐heterocyclic carbene (NHC)/copper cooperative catalysis has enabled

  催化动力学拆分（KR）和动态动力学不对称转化（DyKAT）是获取原料和反应产物的手性立体异构体的替代途径和补充途径。因此，用于动力学控制方法的高效手性催化系统的开发一直是不对称合成的关键之一。N-杂环卡宾（NHC）/铜协同催化作用通过与异黄酮衍生的Enals进行[3 + 3]环化，使外消旋N-甲苯磺酰氮丙啶具有高效的KR和DyKAT，从而导致高度对映体富集的N-甲苯磺酰氮丙啶衍生物（高达99％以上）ee）和具有高结构多样性和立体选择性（最大> 95：5 dr，> 99％的螺环吲哚衍生物的大型文库）ee）。机理研究表明，NHC可以可逆地与铜催化剂结合，而不会损害其催化活性并调节铜络合物的催化活性，从而在KR和DyKAT之间切换化学选择。
• Cu(I)-Catalyzed Enantioselective Friedel–Crafts Alkylation of Indoles with 2-Aryl-<i>N</i>-sulfonylaziridines as Alkylating Agents
  作者：Chen Ge、Ren-Rong Liu、Jian-Rong Gao、Yi-Xia Jia

  DOI：10.1021/acs.orglett.6b01317

  日期：2016.7.1

  A highly enantioselective Friedel–Crafts alkylation of indoles with N-sulfonylaziridines as alkylating agents has been developed by utilizing the complex of Cu(CH3CN)4BF4/(S)-Segphos as a catalyst. A range of optically active tryptamine derivatives are obtained in good to excellent yields and enantioselectivities (up to >99% ee) via a kinetic resolution process.

  通过使用Cu（CH 3 CN）4 BF 4 /（S）-Segphos的配合物，开发了一种以N-磺酰基氮丙啶为烷基化剂的吲哚类高对映选择性的Friedel-Crafts烷基化方法。通过动力学拆分方法以良好至极好的收率和对映选择性（高达> 99％ee）获得了一系列旋光性色胺。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AZIRIDINES AND AMINES, COMPLEXES USED IN THE PROCESS, AND INTERMEDIATES THEREOF
  申请人：Japan Science and Technology Agency

  公开号：EP1767524B1

  公开（公告）日：2013-05-22