(2R,3S)-2-methoxy-2H-spiro-[benzofuran-3,4'-oxazolidin]-2'-one | 1609388-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (2R,3S)-2-methoxy-2H-spiro-[benzofuran-3,4'-oxazolidin]-2'-one
• 英文别名: tert-butyl (2'R,4S)-2'-methoxy-2-oxospiro[1,3-oxazolidine-4,3'-2H-1-benzofuran]-3-carboxylate
• CAS: 1609388-01-3
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: ATVPKMBJXZUEOO-MLGOLLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (2R,3S)-2-methoxy-2H-spiro[benzofuran-3,4'-oxazolidin]-2'-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2R,3S)-2-methoxy-2H-spiro-[benzofuran-3,4'-oxazolidin]-2'-one
  参考文献：
  名称：

  Enantioselective Intramolecular Aza-Spiroannulation onto Benzofurans Using Chiral Rhodium Catalysis

  摘要：

  The development of efficient and enantioselective intramolecular aza-spiroannulation onto benzofurans using chiral rhodium catalysis is described. The optimized reaction conditions [Rh-2(S-TCPTAD)(4) (3 mol %), PhIO (1.6 equiv), MeOH (10 equiv) in PhCF3, 0 degrees C] brought about oxidative aza-spiroannulation of 3-(carbamoylmethyl)benzofuran (3) resulting in (2R,3S)-2-methoxy-2H-spiro-[benzofuran-3,4'-oxazolidin]-2'-one (15a) in 69% yield with 86% ee, the absolute structure of which was determined by a combination of X-ray crystallography and vibrational circular dichroism (VCD) spectroscopy. The reaction is applicable to the asymmetric construction of various 2,3-dihydrobenzofuran derivatives bearing a nitrogen-containing tetrasubstituted carbon stereocenter at C3 (up to 92% ee).

  DOI：

  10.3987/com-14-12941

文献信息

• Enantioselective Intramolecular Aza-Spiroannulation onto Benzofurans Using Chiral Rhodium Catalysis
  作者：Yoshiharu Iwabuchi、Takuro Shibuta、Shigeki Sato、Masatoshi Shibuya、Naoki Kanoh、Tohru Taniguchi、Kenji Monde

  DOI：10.3987/com-14-12941

  日期：——

  The development of efficient and enantioselective intramolecular aza-spiroannulation onto benzofurans using chiral rhodium catalysis is described. The optimized reaction conditions [Rh-2(S-TCPTAD)(4) (3 mol %), PhIO (1.6 equiv), MeOH (10 equiv) in PhCF3, 0 degrees C] brought about oxidative aza-spiroannulation of 3-(carbamoylmethyl)benzofuran (3) resulting in (2R,3S)-2-methoxy-2H-spiro-[benzofuran-3,4'-oxazolidin]-2'-one (15a) in 69% yield with 86% ee, the absolute structure of which was determined by a combination of X-ray crystallography and vibrational circular dichroism (VCD) spectroscopy. The reaction is applicable to the asymmetric construction of various 2,3-dihydrobenzofuran derivatives bearing a nitrogen-containing tetrasubstituted carbon stereocenter at C3 (up to 92% ee).