(R)-N-(1-phenyl-3-butenyl)benzenesulfonamide | 851727-29-2

• 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: (R)-N-(1-phenyl-3-butenyl)benzenesulfonamide
• 英文别名: N-(1-phenylbut-3-enyl)benzenesulfonamide；N-[(1R)-1-phenylbut-3-enyl]benzenesulfonamide
• CAS: 851727-29-2
• 化学式: C₁₆H₁₇NO₂S
• 分子量: 287.382
• InChiKey: GPJHQGLSPSBTQG-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-(1-phenyl-3-butenyl)benzenesulfonamide 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 (1R)-1-苯基-3-丁烯-1-胺
  参考文献：
  名称：

  Synthesis and Catalytic Application of Chiral 1,1‘-Bi-2-naphthol- and Biphenanthrol-Based Pincer Complexes:  Selective Allylation of Sulfonimines with Allyl Stannane and Allyl Trifluoroborate

  摘要：

  New easily accessible 1,1'-bi-2-naphthol- (BINOL-) and biphenanthrol-based chiral pincer complex catalysts were prepared for selective (up to 85% enantiomeric excess) allylation of sulfonimines. The chiral pincer complexes were prepared by a flexible modular approach allowing an efficient tuning of the selectivity of the catalysts. By employment of the different enantiomeric forms of the catalysts, both enantiomers of the homoallylic amines could be selectively obtained. Both allyl stannanes and allyl trifluoroborates can be employed as allyl sources in the reactions. The biphenanthrol-based complexes gave higher selectivity than the substituted BINOL-based analogues, probably because of the well-shaped chiral pocket generated by employment of the biphenanthrol complexes. The enantioselective allylation of sulfonimines presented in this study has important implications for the mechanism given for the pincer complex-catalyzed allylation reactions, confirming that this process takes place without involvement of palladium(0) species.

  DOI：

  10.1021/jo070288b
• 作为产物：
  描述：

  N-苯亚甲基苯磺酰胺 、 烯丙基三丁基锡 在 palladium (chiral biphenanthrol)-based pincer complex 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成 (R)-N-(1-phenyl-3-butenyl)benzenesulfonamide 、 (S)-N-(1-phenyl-3-butenyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Catalytic Application of Chiral 1,1‘-Bi-2-naphthol- and Biphenanthrol-Based Pincer Complexes:  Selective Allylation of Sulfonimines with Allyl Stannane and Allyl Trifluoroborate

  摘要：

  New easily accessible 1,1'-bi-2-naphthol- (BINOL-) and biphenanthrol-based chiral pincer complex catalysts were prepared for selective (up to 85% enantiomeric excess) allylation of sulfonimines. The chiral pincer complexes were prepared by a flexible modular approach allowing an efficient tuning of the selectivity of the catalysts. By employment of the different enantiomeric forms of the catalysts, both enantiomers of the homoallylic amines could be selectively obtained. Both allyl stannanes and allyl trifluoroborates can be employed as allyl sources in the reactions. The biphenanthrol-based complexes gave higher selectivity than the substituted BINOL-based analogues, probably because of the well-shaped chiral pocket generated by employment of the biphenanthrol complexes. The enantioselective allylation of sulfonimines presented in this study has important implications for the mechanism given for the pincer complex-catalyzed allylation reactions, confirming that this process takes place without involvement of palladium(0) species.

  DOI：

  10.1021/jo070288b

文献信息

• Palladium-catalyzed asymmetric umpolung allylation of imines with allylic alcohols
  作者：Xiang-Chen Qiao、Shou-Fei Zhu、Wang-Qiao Chen、Qi-Lin Zhou

  DOI：10.1016/j.tetasy.2010.03.003

  日期：2010.5

  A palladium-catalyzed asymmetric umpolung allylation reaction of imines with allylic alcohols has been developed. In the presence of chiral spiro phosphoramidite ligand 4, the allylation was accomplished with high yields and good enantioselectivities. The use of highly stable and easily available allylic alcohols instead of allylic metal reagents facilitated the preparation of chiral homoallylic amines

  已开发出钯催化的亚胺与烯丙醇的不对称聚烯丙基烯丙基化反应。在手性螺亚磷酰胺配体4的存在下，烯丙基化以高收率和良好的对映选择性完成。使用高度稳定且易于获得的烯丙基醇代替烯丙基金属试剂有助于制备手性均烯丙基胺。
• Synthesis and Catalytic Application of Chiral 1,1‘-Bi-2-naphthol- and Biphenanthrol-Based Pincer Complexes:  Selective Allylation of Sulfonimines with Allyl Stannane and Allyl Trifluoroborate
  作者：Juhanes Aydin、K. Senthil Kumar、Mahmoud J. Sayah、Olov A. Wallner、Kálmán J. Szabó

  DOI：10.1021/jo070288b

  日期：2007.6.1

  New easily accessible 1,1'-bi-2-naphthol- (BINOL-) and biphenanthrol-based chiral pincer complex catalysts were prepared for selective (up to 85% enantiomeric excess) allylation of sulfonimines. The chiral pincer complexes were prepared by a flexible modular approach allowing an efficient tuning of the selectivity of the catalysts. By employment of the different enantiomeric forms of the catalysts, both enantiomers of the homoallylic amines could be selectively obtained. Both allyl stannanes and allyl trifluoroborates can be employed as allyl sources in the reactions. The biphenanthrol-based complexes gave higher selectivity than the substituted BINOL-based analogues, probably because of the well-shaped chiral pocket generated by employment of the biphenanthrol complexes. The enantioselective allylation of sulfonimines presented in this study has important implications for the mechanism given for the pincer complex-catalyzed allylation reactions, confirming that this process takes place without involvement of palladium(0) species.