(2R,3R)-2-methyl-1-(4-nitrophenyl)sulfonyl-3-phenylaziridine

• 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: (2R,3R)-2-methyl-1-(4-nitrophenyl)sulfonyl-3-phenylaziridine
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: MFZTTWFHLYNZDG-LKCRCUOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 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：
  91.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-methyl-1-(4-nitrophenyl)sulfonyl-3-phenylaziridine 在 sodium azide 、 水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以98%的产率得到(1R,2S)-N-(2-azido-1-methyl-2-phenyl-ethyl)-4-nitro-benzenesulfonamide
  参考文献：
  名称：

  衍生自氮丙啶的手性有机催化剂的合成：在不对称羟醛反应中的应用。

  摘要：

  我们报告了通过手性氮丙啶与叠氮化物阴离子的区域和立体选择性开环而衍生的一系列新的高效手性有机催化剂的合成。事实证明，该催化剂对于直接与环酮和无环酮在盐水中进行直接不对称羟醛反应非常有效，催化剂负载量为2 mol％，并以极高的收率（高达99％）和对映选择性（高达到> 99％）。所获得的手性羟醛加合物通过便利的途径进一步转化为手性氮杂环丁烷环。

  DOI：

  10.1021/jo8019863
• 作为产物：
  描述：

  4-硝基苯磺酰胺 在 C₄₂H₇₄FeN₆Si₂⁽²⁺⁾*2ClO₄^(1-) 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.5h， 生成 (2R,3R)-2-methyl-1-(4-nitrophenyl)sulfonyl-3-phenylaziridine
  参考文献：
  名称：

  铁（MCP）配合物以烯烃作为限制试剂催化叠氮化

  摘要：

  本文描述了由铁N，N'-二甲基-N，N'-双（2-吡啶基甲基）环己烷-1,2-二胺-（MCP-）和2-（{{ -[[（吡啶-2-基甲基）吡咯烷-2-基]吡咯烷-1-基}甲基）吡啶型（PDP-型）复合物。这些催化剂基于烯烃底物的有限量，在温和条件下影响苯乙烯的叠氮化。

  DOI：

  10.1021/acs.joc.8b00402

文献信息

• Nitrene Transfer Reactions Catalyzed by Gold Complexes
  作者：Zigang Li、Xiangyu Ding、Chuan He

  DOI：10.1021/jo060016t

  日期：2006.8.1

  We report here the first gold-catalyzed nitrene transfer reaction. A gold(I) compound, supported by 4,4‘,4‘ ‘-tri-tert-butyl-2,2‘:6‘,2‘ ‘-terpyridine (tBu3tpy) as the ligand, efficiently catalyzes olefin aziridination with the use of the commercially available oxidant PhI(OAc)2 and sulfonamides. This system also mediates carbene insertion into benzene.

  我们在这里报告了第一个金催化的腈转移反应。由4,4'，4''-三叔丁基-2,2'：6'，2'-叔吡啶（t Bu 3 tpy）担载的金（I）化合物有效催化烯烃使用可商购的氧化剂PhI（OAc）2和磺酰胺进行叠氮化。该系统还介导卡宾插入苯中。
• A method for rhodium(II)-catalyzed aziridination of olefins
  作者：Paul Müller、Corine Baud、Yvan Jacquier

  DOI：10.1016/0040-4020(95)00999-x

  日期：1996.1

  decomposition of (N-(p-nitrobenzenesulfonyl)imino)phenyliodinane (PhINNs) in the presence of olefins affords aziridines in yields of 18–85%. The aziridination of cis-β- methylstyrene (1h) and cis-hex-2-ene (1k) is stereospecific. However, with cis-stilbene (1m) a ca. 3:1 mixture of cis- and trans aziridines 2m and 21 is obtained. With chiral catalysts asymmetric inductions in up to 73% ee are obtained

  [Rh 2（OAc）4 ]在烯烃存在下催化分解（N-（对硝基苯磺酰基）亚氨基）苯基碘丁烷（PhINNs），得到的氮丙啶为18-85％。的氮杂环丙烷顺式-β-甲基苯乙烯（1H）和顺式-己-2-烯（1K）是立体有择的。但是，使用顺二苯乙烯（1m）时，获得顺式和反式氮丙啶2m和21的3∶1混合物。使用手性催化剂，可获得高达73％ee的不对称诱导。
• The rhodium(II)-catalyzed aziridination of olefins with {[(4-nitrophenyl)sulfonyl]imino}phenyl-lambda<sup>3</sup>-iodane
  作者：Paul Müller、Corine Baud、Yvan Jacquier

  DOI：10.1139/cjc-76-6-738

  日期：——

  The aziridination of olefins with (4-nitrophenylsulfonyl)imino)phenyl-lambda(3)-iodane, NsN=IPh (1c), in the presence of [Rh-2(OAc)(4)] proceeds in yields of up to 85% when the olefin is used in large excess. Under optimized conditions, styrene (4a) is aziridinated with 1 equiv. of NsN=IPh (1c) in 64% yield with 2 mol% of catalyst. The aziridines derived from electron-rich olefins undergo ring-opening under the conditions of the aziridination and afford rearrangement products or pyrrolidines. The aziridination is sterospecific with 1,2-dialkyl- and 1,2-arylalkyl-disubstituted olefins, but nonstereospecific with stilbene. The rho-value for aziridination of substituted styrenes is -0.61. No ring-opened products are observed upon aziridination of vinylcyclopropanes. Tn the presence of chiral Rh-II catalysts, the aziridination is enantioselective, affording an ee of 73% with cis-beta-methylstyrene (4k) and Pirrungs [Rh-2(R)-(-)-bnp}(4)] catalyst. The experimental results are consistent with a one-step mechanism for transfer of the nitrenoid moiety from the catalyst to the olefin.
• Rhodium(II)-catalyzed aziridinations and CH insertions with [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane
  作者：Paul M�ller、Corine Baud、Yvan Jacquier、Mary Moran、Ivo N�geli

  DOI：10.1002/(sici)1099-1395(199606)9:6<341::aid-poc791>3.0.co;2-5

  日期：1996.6

  The [Rh-2(OAc)(4)]-catalyzed decomposition of NsN=IPh [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane} in the presence of olefins affords aziridines in yields of up to 85%. The aziridination of cis-hex-2-ene and cis-beta- methylstyrene is stereospecific, but, cis-stilbene affords a 3:1 mixture of cis- and trans-aziridines in low yield. With chiral Rh(II) catalysts, optically active aziridines are formed having enantiomeric excesses of up to 73%. The NsN=IPh-[Rh-2(OAc)(4)] system is also efficient for the allylic amination of olefins and for insertion into CH bonds, activated by phenyl or oxygen substituents.
• Readily available nitrene precursors increase the scope of Evans' asymmetric aziridination of olefins
  作者：Mikael J. Södergren、Diego A. Alonso、Pher G. Andersson

  DOI：10.1016/s0957-4166(97)00496-5

  日期：1997.11

  The performance of the copper-catalyzed asymmetric aziridination of olefins is highly dependent on the properties of the nitrene precursor. Our preliminary results show significant improvements of both enantioselectivity and chemical yields when [N-(4-nitrobenzenesulfonyl)imino] phenyliodinane 1b (p-NO2C6H4SO2N=IPh) is employed instead of the commonly used p-tolyl analog 1a (PhI=NTs). This paper reports the comparison of some nitrene precursors for the copper-catalyzed asymmetric aziridination of olefins, utilizing the olefin as the limiting component and 1.5 equivalents of the nitrene precursor. The aziridine derivatives of several olefins were obtained in moderate to excellent yields and with enantioselectivity up to 95% ee. (C) 1997 Elsevier Science Ltd.