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Asymmetric Transfer Hydrogenation of ω -Bromo Acetophenones in Aqueous Media
  • ISSN号:1005-1511
  • 期刊名称:《合成化学》
  • 时间:0
  • 分类:O6[理学—化学]
  • 作者机构:[1]Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China
  • 相关基金:We are grateful for the financial support of the National Natural Science Foundation of China (No.203900507, 20025205).
中文摘要:

Optical active ω-bromophenylethanols are useful building blocks for synthesis of various pharmaceuticals such as α 1-, β 2-, and β 3- adrenergic receptor agonists, which are always obtained though a biotransformative pathway and using boron reagent with rigorous conditions [1]. To our knowledge, the metal-catalysed transfer hydrogenation is seldom applied in this reaction. Recently we have developed a water-soluble chiral Ru-complex and applied successfully in transfer hydrogenation of ω-bromo acetophenones in aqueous media [2], which can not be performed in homogeneous system with HCOOH/NEt3 as hydrogen donor[3] .In this paper, we will report that asymmetric transfer hydrogenation of ω-bromo acetophenones was successfully performed in aqueous media by employing hydrophobic Rh-amido complex (TsDPEN-Rh) as catalyst and HCOONa as hydrogen donor. Moreover, marked increasing of activity and high enantioselectivity (up to 98%) of ω-bromo acetophenone 1a was found in the presence of different micelles or vesicles. This method was also applied successfully in preparation of the important chiral medicinal intermediates, such as the precursor of salbutamol, 2b and fermoterol, 2c with high enantioselectivity.

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期刊信息
  • 《合成化学》
  • 中国科技核心期刊
  • 主管单位:四川省科学技术协会
  • 主办单位:四川省化学化工学会 中国科学院成都有机化学有限公司
  • 主编:熊成东
  • 地址:成都市武侯区人民南路四段9号
  • 邮编:610041
  • 邮箱:hchx@cioc.ac.cn
  • 电话:028-85255007
  • 国际标准刊号:ISSN:1005-1511
  • 国内统一刊号:ISSN:51-1427/O6
  • 邮发代号:62-196
  • 获奖情况:
  • 1998年上C.A千名表(803位),1999年入选《中国科学引文数据库》来源期刊,1999-2002年作为《中国学术期刊综合评价数据库》...
  • 国内外数据库收录:
  • 美国化学文摘(网络版),中国中国科技核心期刊,中国北大核心期刊(2008版),中国北大核心期刊(2011版),英国英国皇家化学学会文摘
  • 被引量:7579