(3aR,9aS)-1,3-Diacetyl-1,3,3a,9a-tetrahydro-4,9-dioxa-1,3-diaza-cyclopenta[b]naphthalen-2-one | 827045-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aR,9aS)-1,3-Diacetyl-1,3,3a,9a-tetrahydro-4,9-dioxa-1,3-diaza-cyclopenta[b]naphthalen-2-one
• CAS: 827045-29-4
• 化学式: C₁₃H₁₂N₂O₅
• 分子量: 276.249
• InChiKey: CYPDAWYCTGQVHE-TXEJJXNPSA-N

反应信息

• 作为反应物：
  描述：

  (3aR,9aS)-1,3-Diacetyl-1,3,3a,9a-tetrahydro-4,9-dioxa-1,3-diaza-cyclopenta[b]naphthalen-2-one 在 dimethyl sulfide borane 、 (-)-aminoalcohol compound 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (3aR,9aS)-1-Acetyl-1,3,3a,9a-tetrahydro-4,9-dioxa-1,3-diaza-cyclopenta[b]naphthalen-2-one 、 (3aS,9aR)-1-Acetyl-1,3,3a,9a-tetrahydro-4,9-dioxa-1,3-diaza-cyclopenta[b]naphthalen-2-one
  参考文献：
  名称：

  Catalytic dissymmetrization of meso-2-imidazolidinones: alternative route to chiral synthons for 1,2-diamines

  摘要：

  The chiral functionalization of a simple heterocycle, 1,3-dihydro-2-imidazolone, was achieved by the highly enantioselective monodeacylation of meso-1,3-diacetyl-2-imidazolidinones via an oxazaborolidine-catalyzed borane reduction. This kinetically controlled dissymmetrization is sufficiently effective to provide a synthetic route to either enantiomer of (4S, 5s)- or (4R, 5R)-4,5-dimethoxy-2-imidazolidinone derivatives, which serve as chiral synthons for threo-1,2-diamines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.129
• 作为产物：
  描述：

  邻苯二酚 在 4-二甲氨基吡啶 、 BF*OEt₂ 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3aR,9aS)-1,3-Diacetyl-1,3,3a,9a-tetrahydro-4,9-dioxa-1,3-diaza-cyclopenta[b]naphthalen-2-one
  参考文献：
  名称：

  Catalytic dissymmetrization of meso-2-imidazolidinones: alternative route to chiral synthons for 1,2-diamines

  摘要：

  The chiral functionalization of a simple heterocycle, 1,3-dihydro-2-imidazolone, was achieved by the highly enantioselective monodeacylation of meso-1,3-diacetyl-2-imidazolidinones via an oxazaborolidine-catalyzed borane reduction. This kinetically controlled dissymmetrization is sufficiently effective to provide a synthetic route to either enantiomer of (4S, 5s)- or (4R, 5R)-4,5-dimethoxy-2-imidazolidinone derivatives, which serve as chiral synthons for threo-1,2-diamines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.129