(S_S,2S)-2-methyl-propane-2-sulfinic acid [2-(tert-butyl-dimethyl-silanyloxy)-propylidene]-amide | 638211-43-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S_S,2S)-2-methyl-propane-2-sulfinic acid [2-(tert-butyl-dimethyl-silanyloxy)-propylidene]-amide
• 英文别名: (+)-(S)-N-((S,E)-2-((tert-butyldimethylsilyl)oxy)propylidene)-2-methylpropane-2-sulfinamide；(+)-(S,E)-N-((S)-2-((tert-butyldimethylsilyl)oxy)propylidene)-2-methylpropane-2-sulfinamide；(NE,S)-N-[(2S)-2-[tert-butyl(dimethyl)silyl]oxypropylidene]-2-methylpropane-2-sulfinamide
• CAS: 638211-43-5
• 化学式: C₁₃H₂₉NO₂SSi
• 分子量: 291.53
• InChiKey: HFLNHTUZDVDVHN-NBLDHWDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S_S,2S)-2-methyl-propane-2-sulfinic acid [2-(tert-butyl-dimethyl-silanyloxy)-propylidene]-amide 在 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (+)-tert-butyl ((2S,3R)-2-((tert-butyldimethylsilyl)oxy)hex-5-en-3-yl)carbamate
  参考文献：
  名称：

  N-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation

  摘要：

  A Pd(II)/bis-sulfoxide/Bronsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and pi-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.

  DOI：

  10.1021/ja506036q
• 作为产物：
  描述：

  (S)-2-(叔丁基-二甲基-锡氧基)-丙醛 、 S-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 24.08h， 以73%的产率得到(S_S,2S)-2-methyl-propane-2-sulfinic acid [2-(tert-butyl-dimethyl-silanyloxy)-propylidene]-amide
  参考文献：
  名称：

  N-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation

  摘要：

  A Pd(II)/bis-sulfoxide/Bronsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and pi-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.

  DOI：

  10.1021/ja506036q

文献信息

• Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to <i>N</i>-<i>tert</i>-Butanesulfinyl α-Alkoxyaldimines
  作者：Jared W. Evans、Jonathan A. Ellman

  DOI：10.1021/jo035224p

  日期：2003.12.1

  N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.