[2R,3R,4R,(S)R]-4-(4-bromophenyl)-1-(tert-butylsulfinyl)-3-methyl-4-(4-methylphenylsulfonamido)butan-2-yl acetate | 1215087-90-3

• 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: [2R,3R,4R,(S)R]-4-(4-bromophenyl)-1-(tert-butylsulfinyl)-3-methyl-4-(4-methylphenylsulfonamido)butan-2-yl acetate
• CAS: 1215087-90-3
• 化学式: C₂₄H₃₂BrNO₅S₂
• 分子量: 558.558
• InChiKey: CXNYTXMITDIGOX-VQNVXJIESA-N

反应信息

• 作为产物：
  描述：

  [1RS,2RS,(S)R]-N-(1-(4-bromophenyl)-4-(tert-butylsulfinyl)-3-hydroxy-2-methylbutyl)-4-methylphenylsulfonamide 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以66%的产率得到[2R,3R,4R,(S)R]-4-(4-bromophenyl)-1-(tert-butylsulfinyl)-3-methyl-4-(4-methylphenylsulfonamido)butan-2-yl acetate
  参考文献：
  名称：

  SmI2-coupling reaction of chiral non-racemic α-bromo-α′-sulfinyl ketones with imines: synthesis of enantiomerically pure 2-methyl-3-amino-1-ol moieties

  摘要：

  Chiral non-racemic alpha-bromo-alpha'-sulfinyl ketones were shown to react with imines in the presence of SmI2 to give the corresponding 1,3-aminoketo derivatives with good syn-diastereoselectivity. Further reduction of these adducts either with DIBAL-H only or with DIBAL-H in the presence of Yb(OTf)(3) afforded syn- and anti-2-methyl-3-amino-1-ol moieties, respectively, in good yields and diastereoselectivities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.020