(R)-(-)-N-(1-phenylethylidene)-2-methylpropanesulfinamide

• 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-phenylethylidene)-2-methylpropanesulfinamide
• 英文别名: (NZ,R)-2-methyl-N-(1-phenylethylidene)propane-2-sulfinamide
• 化学式: C₁₂H₁₇NOS
• 分子量: 223.339
• InChiKey: ZLLYZGSBXIAKFQ-VSKPTYQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苄叉丙酮 、 (R)-(-)-N-(1-phenylethylidene)-2-methylpropanesulfinamide 在 正丁基锂 、 二异丙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 22.75h， 以60%的产率得到(NZ,R)-2-methyl-N-[(3R)-5-oxo-1,3-diphenylhexylidene]propane-2-sulfinamide
  参考文献：
  名称：

  N-Sulfinyl Metalloenamine Conjugate Additions:  Asymmetric Synthesis of Piperidines

  摘要：

  [GRAPHICS]The first examples of conjugate additions of N-tert-butanesulfinyl metalloenamines are reported. Highly stereoselective conjugate additions (97:3 to 99:1 dr) were observed between metalloenamines derived from N-sulfinyl ketimines and alpha,beta-unsaturated ketones bearing either alkyl or aryl substituents. The conjugate addition products could rapidly be converted with high diastereoselectivity to 2,4,6-trisubstituted piperidines, which are difficult to access by other methods.

  DOI：

  10.1021/jo051020s

文献信息

• Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines
  作者：Derek A. Cogan、Guangcheng Liu、Jonathan Ellman

  DOI：10.1016/s0040-4020(99)00451-2

  日期：1999.7

  High yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert-butanesulfinyl ketimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6)

  对于有机金属试剂的1,2-增补高产量和高立体选择性的方法ñ -叔-butanesulfinyl醛亚胺（2）和Ñ -叔-butanesulfinyl酮亚胺（3）中描述。已证明将烷基，芳基，烯基和烯丙基碳负离子添加到具有不同空间和电子特性的各种亚胺中。亚磺酰胺产物（4和6）的酸性甲醇分解可提供高度对映体富集的α-支化和α，α-二支化胺。由于很容易从醛和酮中获得广泛的亚磺酰基亚胺，因此可以制备多种对映体富集的胺。
• <i>N</i>-Sulfinyl Metalloenamine Conjugate Additions:  Asymmetric Synthesis of Piperidines
  作者：Hillary M. Peltier、Jonathan A. Ellman

  DOI：10.1021/jo051020s

  日期：2005.9.1

  [GRAPHICS]The first examples of conjugate additions of N-tert-butanesulfinyl metalloenamines are reported. Highly stereoselective conjugate additions (97:3 to 99:1 dr) were observed between metalloenamines derived from N-sulfinyl ketimines and alpha,beta-unsaturated ketones bearing either alkyl or aryl substituents. The conjugate addition products could rapidly be converted with high diastereoselectivity to 2,4,6-trisubstituted piperidines, which are difficult to access by other methods.