methyl 2-(3-tosyloxazolidin-2-yl)acetate | 1265900-20-6

• 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: methyl 2-(3-tosyloxazolidin-2-yl)acetate
• CAS: 1265900-20-6
• 化学式: C₁₃H₁₇NO₅S
• 分子量: 299.348
• InChiKey: LKWLVHVIHIPUHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 在 双(乙腈)氯化钯(II) 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 2-(3-tosyloxazolidin-2-yl)acetate
  参考文献：
  名称：

  2,2-Difunctionalization of Alkenes via Pd(II)-Catalyzed Aza-Wacker Reactions

  摘要：

  N-Ts and N-Boc derivatives of 1,2-diamines and 1,2-amino alcohols are shown to undergo efficient Pd(II)-catalyzed aza-Wacker reactions with a large range of electron-deficient alkenes. The resulting enamine intermediate generally undergoes cyclization with the second heteroatom to form 1,3-heterocycles. The sequence facilitates the rapid synthesis of saturated oxazolidines, imidazolidines, and their derivatives. Use of N-L-valinol derivatives results in highly diastereoselective reactions, where the net stereochemical outcome diverges between N-Ts and N-Boc.

  DOI：

  10.1021/ol102956x

文献信息

• Palladium-catalyzed oxamidation of alkenes: A new approach to benzoxazolidines
  作者：Niranjan Panda、Sushree Arpitabala Yadav

  DOI：10.1016/j.tet.2018.02.012

  日期：2018.3

  A novel palladium catalyzed protocol for the synthesis of benzoxazolidine by the reaction sulfamidophenol and terminal alkene was developed. This oxamidation process is simple and does not require any ligand, base or inert atmosphere for the overall transformation. From control experiments, it is apparent that the cross-coupling reaction proceeds with initial formation of enesulfonamide which undergoes

  提出了一种新的钯催化方案，其通过磺酰胺基苯酚和末端烯烃的反应合成苯并恶唑烷。该乙酰胺化过程很简单，不需要任何配体，碱或惰性气氛即可进行整体转化。从对照实验中可以明显看出，交叉偶联反应是随着烯磺酰胺的初步形成而进行的，该烯磺酰胺通过分子内的环化反应而被核仁酸化，随后被TsOH进行原去palpalpalpal化，从而得到苯并恶唑烷。
• Aza-Wacker-Type Reaction between Electron-Deficient Olefins and <i>N</i>-Alkylsulfonamides
  作者：Huayou Hu、Jiaxin Tian、Yun Liu、Yong Liu、Fei Shi、Xiang Wang、Yuhe Kan、Chao Wang

  DOI：10.1021/jo502823m

  日期：2015.3.6

  A palladium-catalyzed oxidative amination protocol of electron-deficient olefins by aza-Wacker-type reaction with N-alkylsulfonamides was developed. The presence of the stoichiometric amount of methanesulfonic acid was crucial for the success of this transformation. The reactions were conducted in green solvent under mild conditions and scalable with excellent E-type stereoselectivity. In addition, a Pd(II)/Pd(0) catalytic cycle with the existence of a very strong oxidant (Selectfluor) was proposed.