(1S,2R)-6,7-dibromo-2-(3-methylphenyl)-1,2-dihydronaphthalen-1-ol | 1505513-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: (1S,2R)-6,7-dibromo-2-(3-methylphenyl)-1,2-dihydronaphthalen-1-ol
• CAS: 1505513-95-0
• 化学式: C₁₇H₁₄Br₂O
• 分子量: 394.106
• InChiKey: GGAKLSPOPQAGMO-DYVFJYSZSA-N

反应信息

• 作为产物：
  描述：

  3-甲基苯硼酸 、 6,7-dibromo-1,4-dihydro-1,4-epoxynaphthalene 在 bis(1,5-cyclooctadiene)nickel (0) 、 (+)-1,2-双((2S,5S)-2,5-二甲基磷烷)苯 、 potassium hydroxide 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以97%的产率得到(1S,2R)-6,7-dibromo-2-(3-methylphenyl)-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  Nickel-Catalyzed Asymmetric Ring Opening of Oxabenzonorbornadienes with Arylboronic Acids

  摘要：

  A new, versatile, and highly efficient nickel-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of arylboronic acids has been developed, yielding cis-2-aryl-1,2-dihydronaphthalen-1-ols in high yields (up to 99%) with good to excellent enantioselectivities (up to 99% ee) under very mild conditions. The effects of various nickel precursors, chiral bidentate ligands, catalyst loadings, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding cis-ring-opened products based on the X-ray structure of product 4b.

  DOI：

  10.1021/jo500821m

文献信息

• Platinum(II)-Catalyzed Asymmetric Ring-Opening Addition of Arylboronic Acids to Oxabenzonorbornadienes
  作者：Xuejing Pan、Guobao Huang、Yuhua Long、Xiongjun Zuo、Xuan Xu、Fenglong Gu、Dingqiao Yang

  DOI：10.1021/jo402386k

  日期：2014.1.3

  A new platinum(II)-catalyzed asymmetric ring-opening addition of arylboronic acids to oxabenzonorbornadienes was developed, which afforded the corresponding cis-2-aryl-1,2-dihydronaphthalen-1-ol products in high yields (up to 97%) with moderate to good enantioselectivities (up to 89% ee) under very mild conditions. The effects of various ligands, catalyst loading, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. The cis configuration of product 2m was confirmed by X-ray diffraction analysis. A potential mechanism for the present catalytic reaction is proposed.