(+/-)-cis-2-methyl-3,6-diphenyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (+/-)-cis-2-methyl-3,6-diphenyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 2-methyl-3,6-diphenyl-1,2-oxazinane-4,4-dicarboxylate；dimethyl (3S,6S)-2-methyl-3,6-diphenyloxazinane-4,4-dicarboxylate
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: AMPCDPVWUXNDLW-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-cis-2-methyl-3,6-diphenyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Diastereoselective Synthesis of Pyrrolidines Using a Nitrone/Cyclopropane Cycloaddition:  Synthesis of the Tetracyclic Core of Nakadomarin A

  摘要：

  The synthesis of the tetracyclic core of nakadomarin A is described. The core contains all the heterocycles and the required stereocenters found in the natural product and provides a promising route to the target itself. The strategy utilizes a general, diastereoselective pyrrolidine synthesis that proceeds via a homo 3+2 dipolar cycloaddition. The scope of this methodology is also described.

  DOI：

  10.1021/ol0501018
• 作为产物：
  描述：

  2-苯基环丙烷-1,1-二甲酸二甲酯 、 N-methyl-α-phenylnitrone 在 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以84%的产率得到(+/-)-cis-2-methyl-3,6-diphenyl-[1,2]oxazinane-4,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Enantioselective Addition of Nitrones to Activated Cyclopropanes

  摘要：

  In this paper, we demonstrate the first examples of chiral Lewis acid catalysis in the formation of tetrahydro-1,2-oxazines with very high enantioselectivity starting with diactivated cyclopropanes and nitrones (>90% yields and ee). Reactions with racemic substituted cyclopropanes provide approximately 1:1 diastereomeric tetrahydro-1,2-oxazine products with high enantioselectivity. Mechanistic information for the formation of the tetrahydro-1,2-oxazines is also detailed.

  DOI：

  10.1021/ja0421497

文献信息

• The Reaction of Nitrones with Cyclopropanes: A Convenient Preparation of Tetrahydro-1,2-oxazines
  作者：Michael Kerr、Cheryl Carson、Ian Young

  DOI：10.1055/s-2007-990864

  日期：2008.2

  undergo smooth reaction in the presence of ytterbium(III) triflate to form tetrahydro-1,2-oxazines with a high degree of regio- and stereocontrol. A three-component protocol has also been developed wherein the nitrone is generated in situ from an aldehyde and a hydroxylamine. The reactions are often high yielding with broad substrate scope. The multicomponent nature of the reaction makes it amenable

  Nitrones 和 dialkyl cyclopropane-1,1-dicarboxylates 在三氟甲磺酸镱 (III) 的存在下进行平稳反应，形成具有高度区域和立体控制的四氢 1,2-恶嗪。还开发了一种三组分方案，其中硝酮由醛和羟胺原位生成。该反应通常具有高产率和广泛的底物范围。该反应的多组分性质使其适用于化合物库的合成，并且还允许在面向目标的合成中开发高度收敛的策略。
• Diastereoselective 1,3-Dipolar Cycloaddition of Nitrones to Donor–Acceptor Cyclopropanes Catalyzed by a Calcium(II) Complex
  作者：Caroline M. Braun、Elizabeth A. Congdon、Kristine A. Nolin

  DOI：10.1021/jo502686t

  日期：2015.2.6

  Calcium triflate has been identified as an efficient catalyst for the cycloaddition of nitrones to donor-acceptor cyclopropanes. The reaction proceeds with good to excellent yields of the corresponding tetrahydro-1,2-oxazines with high levels of diastereoselectivity. The generality of the reaction allowed for the synthesis of tetrahydro-1,2-oxazines bearing alkyl, aryl, and heteroaromatic substitution.
• Highly Enantioselective and Diastereoselective Cycloaddition of Cyclopropanes with Nitrones and Its Application in the Kinetic Resolution of 2-Substituted Cyclopropane-1,1-dicarboxylates
  作者：Yan-Biao Kang、Xiu-Li Sun、Yong Tang

  DOI：10.1002/anie.200604645

  日期：2007.5.18
• A Homo [3+2] Dipolar Cycloaddition: The Reaction of Nitrones with Cyclopropanes
  作者：Ian S. Young、Michael A. Kerr

  DOI：10.1002/anie.200351573

  日期：2003.7.7