(3R,4R)-1-(4-bromophenyl)-3,4-diphenyl-2-azetidinone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3R,4R)-1-(4-bromophenyl)-3,4-diphenyl-2-azetidinone
• 英文别名: (3R,4R)-1-(4-bromophenyl)-3,4-diphenylazetidin-2-one
• 化学式: C₂₁H₁₆BrNO
• 分子量: 378.268
• InChiKey: ALIJJTJTYQKXGT-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1-溴-4-硝基苯 在 platinum on activated charcoal 、 (+)-(R,R)-bis(hexamethylazaferrocene)methylene 、 copper(l) chloride 甲烷磺酸 、 N-甲基二环己基胺 、 氢气 、 亚磷酸三乙酯 作用下， 以 乙腈 为溶剂， 反应 135.0h， 生成 (3R,4R)-1-(4-bromophenyl)-3,4-diphenyl-2-azetidinone
  参考文献：
  名称：

  Cu(I)/Bis(azaferrocene)-Catalyzed Enantioselective Synthesis of β-Lactams via Couplings of Alkynes with Nitrones

  摘要：

  As a consequence of the wide-ranging significance of beta-lactams (e.g., use as drugs and as chiral building blocks), a great deal of effort has been dedicated to the development of methods for their stereoselective synthesis. Although considerable progress has been achieved, nearly all of the approaches that have been described are based on the use of chiral precursors; direct catalytic enantioselective routes to beta-lactams are rare as well as limited in scope. In this communication, we establish that, using a new C2-symmetric planar-chiral bis(azaferrocene) ligand, we can generate beta-lactams with very good enantiomeric excess and cis diastereoselection via catalytic enantioselective Kinugasa reactions (couplings of alkynes with nitrones). Appealing attributes of this process include the ready availability of the starting materials, the functional-group tolerance of the reaction, and the convergency of the approach.

  DOI：

  10.1021/ja025833z

文献信息

• Chiral tris(oxazoline)/Cu(ii) catalyzed coupling of terminal alkynes and nitronesElectronic supplementary information (ESI) available: experimental. See http://www.rsc.org/suppdata/cc/b3/b306653c/
  作者：Meng-Chun Ye、Jian Zhou、Zheng-Zheng Huang、Yong Tang

  DOI：10.1039/b306653c

  日期：——

  Novel chiral iPr-tris(oxazoline)/Cu(ClO4)2 x 6H2O catalyzed coupling of terminal acetylenes and nitrones to afford cis-disubstituted beta-lactams is described; the choice of base proves essential to both the diastereoselectivity and the enantioselectivity.

  描述了新颖的手性iPr-三（恶唑啉）/ Cu（ClO4）2 x 6H2O催化的末端乙炔和硝酮的偶联，得到顺式二取代的β-内酰胺。碱的选择被证明对非对映选择性和对映选择性都是必不可少的。
• Trisoxazoline/Cu(II)-Promoted Kinugasa Reaction. Enantioselective Synthesis of <i>β</i>-Lactams
  作者：Meng-Chun Ye、Jian Zhou、Yong Tang

  DOI：10.1021/jo0602874

  日期：2006.4.1

  precursor for the first time in the Kinugasa reaction, and this allowed the reaction to be performed under a practical and convenient condition. An appropriate base used in this reaction was essential to control both diastereoselectivity and enantioselectivity. Compared with primary and tertiary amines, secondary amines gave higher enantioselectivities. The reaction scope and limitation as well as the

  手性i催化硝基酮与末端炔烃的反应Pr-三恶唑啉2a / Cu（ClO 4）2 ·6H 2在空气气氛下，以中等至良好的产率提供了高达85％ee的β-内酰胺。非对映选择性取决于炔烃。丙炔酸酯给出反式异构体作为主要产物，而其他炔烃主要提供顺式-二取代的内酰胺。在Kinugasa反应中，铜（II）盐首次被证明是有效的催化剂前体，这使得该反应可以在实用且方便的条件下进行。在该反应中使用的合适的碱对于控制非对映选择性和对映选择性都是必不可少的。与伯胺和叔胺相比，仲胺具有更高的对映选择性。研究了反应的范围和局限性及其机理。
• Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction
  作者：Chuanlong Xu、Yuchen Yang、Yue Wu、Feilong He、Huakang He、Ping Deng、Hui Zhou

  DOI：10.1039/d0ra03276j

  日期：——

  A novel class of chiral N,N,N imine-containing ligands derived from TsDPEN (N-(p-tosyl)-1,2-diphenylethylene-1,2-diamine) has been developed and applied to the copper-catalyzed asymmetric Kinugasa reaction. The copper(II) salt proved to be an efficient catalyst precursor, and it provides an efficient way to synthesize enantioenriched cis-β-lactam. The pathway is air-tolerant and easily manipulated

  开发了一类新型的手性N , N , N亚胺配体，衍生自 TsDPEN ( N -( p -tosyl)-1,2-diphenylethylene-1,2-diamine) 并应用于铜催化的不对称衣笠反应。铜( II )盐被证明是一种高效的催化剂前体，它为合成富含对映体的顺式-β-内酰胺提供了一种有效的途径。该途径耐空气且易于操作，配体易于合成。提出了一个工作模型，其中立体控制步骤是乙烯酮和亚胺之间的 [2 + 2] 环加成，以解释观察到的立体选择性。