(2R,3R)-cis-1-(N-1-bis(4-methoxy-3,5-di-tert-butylphenyl)methyl)-2-carboxyethyl-3-(4-bromophenyl)aziridine | 1072879-29-8

• 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)-cis-1-(N-1-bis(4-methoxy-3,5-di-tert-butylphenyl)methyl)-2-carboxyethyl-3-(4-bromophenyl)aziridine
• 英文别名: ethyl (2R,3R)-1-[bis(3,5-ditert-butyl-4-methoxyphenyl)methyl]-3-(4-bromophenyl)aziridine-2-carboxylate
• CAS: 1072879-29-8
• 化学式: C₄₂H₅₈BrNO₄
• 分子量: 720.831
• InChiKey: HGOHWJZXQKRGCS-LLQYTKIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-cis-1-(N-1-bis(4-methoxy-3,5-di-tert-butylphenyl)methyl)-2-carboxyethyl-3-(4-bromophenyl)aziridine 在 草酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.08h， 生成
  参考文献：
  名称：

  2-氯-2-氧代乙酸酐的多面拦截：β-内酰胺的催化不对称合成†

  摘要：

  氮丙啶-2-羧酸会与 草酰氯根据3-位取代基的性质，得到吗啉-2,3,5-三酮，环状N-羧基酸酐或β-内酰胺。用Vilsmeier试剂处理后，所有底物均可转移至β-内酰胺类。三至四元环的扩环是立体定向的，并以高产率和非对映选择性进行。该方法提供了通过多组分催化不对称叠氮化反应由简单的醛不对称合成β-内酰胺的方法。

  DOI：

  10.1039/c2sc21240d
• 作为产物：
  描述：

  重氮乙酸乙酯 、 N-(4-bromobenzylidene)-bis(4-methoxy-3,5-di-tert-butylphenyl)methylamine 在 三苯基硼酸酯 、 (R)-2,2'-二苯基-3,3'-(4-联菲酚) 作用下， 以 甲苯 为溶剂， 反应 24.08h， 以99%的产率得到(2R,3R)-cis-1-(N-1-bis(4-methoxy-3,5-di-tert-butylphenyl)methyl)-2-carboxyethyl-3-(4-bromophenyl)aziridine
  参考文献：
  名称：

  Mapping the Active Site in a Chemzyme: Diversity in the N-Substituent in the Catalytic Asymmetric Aziridination of Imines

  摘要：

  The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)(3) is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.

  DOI：

  10.1021/ol802431v

文献信息

• Evidence for a Boroxinate Based Brønsted Acid Derivative of VAPOL as the Active Catalyst in the Catalytic Asymmetric Aziridination Reaction
  作者：Gang Hu、Li Huang、Rui H. Huang、William D. Wulff

  DOI：10.1021/ja904589k

  日期：2009.11.4

  Studies are described that were designed to determine the structure of the active catalyst in the asymmetric catalytic aziridination of imines with ethyl diazoacetate (AZ reaction). Evidence suggests that the active catalyst contains a boroxine ring in which one of the three boron atoms is spiro-fused with the two phenol groups of the VAPOL tigand. B-11 and H-1 NMR evidence supports the boroxinate structure B in which the counterion to the boroxinate is the protonated form of the imine. The boroxinate structure is also supported by two solid state structures of a VAPOL boroxinate in which the gegen cation is tetramethyl ammonium and 4-dimethylaminopyridinium.
• Mapping the Active Site in a Chemzyme: Diversity in the <i>N</i>-Substituent in the Catalytic Asymmetric Aziridination of Imines
  作者：Yu Zhang、Zhenjie Lu、Aman Desai、William D. Wulff

  DOI：10.1021/ol802431v

  日期：2008.12.4

  The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)(3) is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.
• Multifaceted interception of 2-chloro-2-oxoacetic anhydrides: a catalytic asymmetric synthesis of β-lactams
  作者：Li Huang、Wenjun Zhao、Richard J. Staples、William D. Wulff

  DOI：10.1039/c2sc21240d

  日期：——

  N-carboxyanhydrides or β-lactams depending on the nature of the substituent at the 3-position. All substrates can be diverted to β-lactams upon treatment with a Vilsmeier reagent. The three to four membered ring expansion is stereospecific and proceeds with high yields and diastereoselection. This method provides for an asymmetric synthesis of β-lactams from simple aldehydes via a multi-component catalytic asymmetric

  氮丙啶-2-羧酸会与 草酰氯根据3-位取代基的性质，得到吗啉-2,3,5-三酮，环状N-羧基酸酐或β-内酰胺。用Vilsmeier试剂处理后，所有底物均可转移至β-内酰胺类。三至四元环的扩环是立体定向的，并以高产率和非对映选择性进行。该方法提供了通过多组分催化不对称叠氮化反应由简单的醛不对称合成β-内酰胺的方法。