(S,S)-3-(o-tolyl)-2-tosyl-1,2-oxaziridine | 73844-92-5

• 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: (S,S)-3-(o-tolyl)-2-tosyl-1,2-oxaziridine
• 英文别名: (S,S)-3-o-tolyl-2-tosyl-1,2-oxaziridine；(S,S)-3-(2-tolyl)-2-tosyloxaziridine
• CAS: 73844-92-5；111556-08-2
• 化学式: C₁₅H₁₅NO₃S
• 分子量: 289.355
• InChiKey: QEFRWPNRSVIUJZ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.68
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-(2-methylphenyl)methylidene-4-methylbenzenesulfonamide 在 C₃₄H₃₄N₂O₂ 、 间氯过氧苯甲酸 作用下， 以 甲苯 为溶剂， 以94%的产率得到(S,S)-3-(o-tolyl)-2-tosyl-1,2-oxaziridine
  参考文献：
  名称：

  Catalytic Enantioselective Oxaziridination

  摘要：

  The first catalytic enantioselective synthesis of oxaziridines is presented. The oxidation of aryl and alkyl aldimines with m-CPBA under organocatalytic conditions using cinchona alkaloid-derived catalysts furnished optically active oxaziridines in good yields and high enantioselectivities (up to 94% ee). Mechanistic investigations indicate a stepwise enantioselective oxidation process.

  DOI：

  10.1021/ja2064457

文献信息

• Kinetic Resolution of Oxaziridines via Chiral Bifunctional Guanidine-Catalyzed Enantioselective α-Hydroxylation of β-Keto Esters
  作者：Xiaobin Lin、Sai Ruan、Qian Yao、Chengkai Yin、Lili Lin、Xiaoming Feng、Xiaohua Liu

  DOI：10.1021/acs.orglett.6b01614

  日期：2016.8.5

  efficient kinetic resolution of racemic oxaziridines has been realized via catalytic asymmetric α-hydroxylation of available β-keto esters. In the presence of a chiral bifunctional guanidine catalyst, a variety of optically active oxaziridines and chiral α-hydroxy β-keto esters were generated with excellent results (ee’s of up to 99% and 97% and yields of up to 44% and 54%, respectively).

  通过可利用的β-酮酯的催化不对称α-羟基化，已经实现了外消旋恶唑烷的有效动力学拆分。在手性双官能胍催化剂的存在下，生成了多种旋光性恶唑烷和手性α-羟基β-酮酸酯，具有优异的结果（ee高达99％和97％，产率高达44％和54％ ， 分别）。
• Organocatalytic Oxyamination of Azlactones: Kinetic Resolution of Oxaziridines and Asymmetric Synthesis of Oxazolin-4-ones
  作者：Shunxi Dong、Xiaohua Liu、Yin Zhu、Peng He、Lili Lin、Xiaoming Feng

  DOI：10.1021/ja404379n

  日期：2013.7.10

  example of oxyamination of azlactones with oxaziridines was realized using a chiral bisguanidinium salt. Efficient catalytic asymmetric oxyamination and kinetic resolution of oxaziridines occurred simultaneously. Various chiral oxazolin-4-one derivatives with potential biological activity were obtained (up to 92% ee). Meanwhile, a series of optically pure oxaziridines were recovered with up to 99% ee and

  使用手性双胍盐实现吖内酯与恶氮丙啶氧胺化的第一个实例。氧氮丙啶的高效催化不对称氧化胺化和动力学拆分同时发生。获得了具有潜在生物活性的各种手性 oxazolin-4-one 衍生物（高达 92% ee）。同时，回收了一系列光学纯氧氮杂环丙烷，ee 高达 99%，并成功用于 3-甲基-1H-吲哚和苯乙烯的不对称氧化胺化。还通过对照实验研究了三重立体分化过程。
• Enantioselective Organocatalytic Oxaziridination of N-Tosyl Aldimine Catalyzed by<i>Cinchona</i>Alkaloid-Ester Derivatives
  作者：Ying Jin、Tianyi Zhang、Wei Zhang、Sheng Chang、Bo Feng

  DOI：10.1002/chir.22283

  日期：2014.3

  A series of cinchona alkaloid‐ester derivatives was synthesized and applied to catalyze the enantioselective oxaziridination of aryl aldimines with m‐CPBA. The (R,R)‐oxaziridines were obtained in good yields with high enantiomeric excess (ee) values (up to 98%). Chirality 26:150–154, 2014. © 2014 Wiley Periodicals, Inc.

  合成了一系列金鸡纳生物碱酯衍生物，并将其用于催化m - CPBA对芳基醛亚胺的对映选择性恶二叠氮化。（R，R）-恶唑烷的收率高，对映体过量（ee）值高（高达98％）。手性26：150–154，2014。©2014 Wiley Periodicals，Inc.
• Asymmetric oxaziridination catalyzed by cinchona alkaloid derivatives containing sulfide
  作者：Tianyi Zhang、Wei He、Xingyu Zhao、Ying Jin

  DOI：10.1016/j.tet.2013.06.061

  日期：2013.9

  A new method has been developed for the asymmetric oxaziridination of aryl aldimines with m-chloroperbenzoic acid, involving the use of cinchona alkaloid derivatives containing a sulfide moiety as a catalyst. The new method provided access to optically active oxaziridines in good yields with high enantiomeric excess (ee) values of up to 95%.

  的新方法已发展为芳基醛亚胺与非对称oxaziridination米氯过苯甲酸，涉及使用金鸡纳含有硫化物基团作为催化剂生物碱衍生物。新方法提供了以高收率获得高达95％的高对映体过量（ee）值的旋光恶唑烷的方法。
• Chemistry of oxaziridines. 1. Synthesis and structure of 2-arenesulfonyl-3-aryloxaziridines. A new class of oxaziridines
  作者：Franklin A. Davis、Joseph Lamendola、Upender Nadir、Edward W. Kluger、Thomas C. Sedergran、Thomas W. Panunto、Robert Billmers、Robert Jenkins、Ignatius J. Turchi

  DOI：10.1021/ja00526a040

  日期：1980.3