(S)-N-{(3S,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-2-methylpropane-2-sulfinamide | 1541176-83-3

• 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: (S)-N-{(3S,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-2-methylpropane-2-sulfinamide
• 英文别名: (S)-N-[(3S,4R)-4-(1-bromoethenyl)-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl]-2-methylpropane-2-sulfinamide
• CAS: 1541176-83-3
• 化学式: C₁₇H₂₅BrN₂O₃S₂
• 分子量: 449.433
• InChiKey: ZPALMWWMNJJITK-DXMSMQRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-{(3S,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-2-methylpropane-2-sulfinamide 、 3-氯-2-甲基丙烯 在 copper(l) iodide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 2.0h， 以78%的产率得到(-)-(S)-2-methyl-N-{(3S,4R)-4-(4-methylpenta-1,4-dien-2-yl)-1-tosylpyrrolidin-3-yl}propane-2-sulfinamide
  参考文献：
  名称：

  Regulation of Diastereoselectivity in the Carbocyclization of Allenyl (S)-N-tert-Butylsulfinimines through a Three-Component Assembly

  摘要：

  Allenyl sulfinimines can be stereoselectively cyclized with hexamethylditin under palladium catalysis conditions followed by a selection of additives for an activated transmetalation. Reactivity and diastereoselectivity for the cyclization strongly depend on the characteristics of additives. A highly diastereoselective synthesis of five-membered rings is achieved from the reaction of the corresponding allenyl (5)-N-tert-butylsulfinimies through the following sequence. After the distannylation of the allenyl group with hexamethylditin catalyzed by the Pd complex, stereochemical routes are additive dependent: addition of SnCl4 affords a cis ring exclusively, whereas a trans ring is formed predominantly by the introduction of B-bromocatecholborane. Extension of the methodology to the synthesis of six-membered cis rings is achieved by using B-bromocatecholborane. Stereochemical relationships of products were unambiguously deduced by X-ray crystallography.

  DOI：

  10.1021/jo4025072
• 作为产物：
  描述：

  (+)-(S)-2-methyl-N-[(3S,4R)-1-tosyl-4-{1-(trimethylstannyl)vinyl}pyrrolidin-3-yl]propane-2-sulfinamide 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以44%的产率得到(S)-N-{(3S,4R)-4-(1-bromovinyl)-1-tosylpyrrolidin-3-yl}-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Regulation of Diastereoselectivity in the Carbocyclization of Allenyl (S)-N-tert-Butylsulfinimines through a Three-Component Assembly

  摘要：

  Allenyl sulfinimines can be stereoselectively cyclized with hexamethylditin under palladium catalysis conditions followed by a selection of additives for an activated transmetalation. Reactivity and diastereoselectivity for the cyclization strongly depend on the characteristics of additives. A highly diastereoselective synthesis of five-membered rings is achieved from the reaction of the corresponding allenyl (5)-N-tert-butylsulfinimies through the following sequence. After the distannylation of the allenyl group with hexamethylditin catalyzed by the Pd complex, stereochemical routes are additive dependent: addition of SnCl4 affords a cis ring exclusively, whereas a trans ring is formed predominantly by the introduction of B-bromocatecholborane. Extension of the methodology to the synthesis of six-membered cis rings is achieved by using B-bromocatecholborane. Stereochemical relationships of products were unambiguously deduced by X-ray crystallography.

  DOI：

  10.1021/jo4025072