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BINOL衍生的手性磷酸催化的不对称反应研究进展 被引量：1

Research Progress in the Asymmetric Reaction Catalyzed by Chiral BINOL Phosphoric Acids
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摘要 综述了近年来BINOL衍生的手性磷酸作为一类强酸性Brφnsted酸催化剂,在不对称氢转移反应、Friedel-Crafts,Mannich,Aza Diels-Alder,Aza-ene-type,Pictet-Spengler等反应中的研究进展。参考文献37篇。 This paper reviews the recent research progress（ 37 references） in the asymmetric reactions catalyzed by chiral phosphoric acids（ derived from BINOL as a class of strongly acidic BrФnsted acid catalyst）. The asymmetric reactions include the transfer hydrogenation reaction, the Friedel-Crafts reaction, the Mannich reaction, the Aza Diels-Alder reaction, the Aza-ene-type reaction, the Pictet- Spengler reaction and so on.
作者 郭海明 李建国 王东超 渠桂荣
机构地区 河南师范大学化学与环境科学学院
出处 《合成化学》 CAS CSCD 北大核心 2009年第3期265-271,共7页 Chinese Journal of Synthetic Chemistry
基金 国家自然科学基金资助项目(20802016)
关键词 手性磷酸 不对称反应 综述 chiral phosphoric acid asymmetric reaction review
分类号 O643.36 [理学—物理化学]
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参考文献37

  • 1Akiyama T, Itoh J, Yokota K, et al. Enantioselective mannich-type reaction catalyzed by a chiral brcnsted acid [ J ]. Angew Chem Int Ed, 2004,43 : 1566 - 1568.
  • 2Uraguchi D, Tereda M. Chiral brcnsted acid-catalyzed direct mannich reactions via electrophilic activation [ J]. J Am Chem Soc ,2004,126:5356 - 5357.
  • 3Hoffmann S, Nieoletti M, List B. Catalytic asymmetric reductive amination of aldehydes via dynamic kinetic resolution[ J]. J Am Chem Soc,2006,128:13074 - 13075.
  • 4Kang Q, Zhao Z A, You S L. Highly enantioselective transfer hydrogenation of ol-imino esters by a phosphoric acid[ J]. Adv Synth Catal,2007.,349 : 1657 - 1660.
  • 5Storer R I, Carrera D E, Ni Y K, et al. Enantioselective organocatalytic reductive amination [ J ]. J Am Chem Soe ,2006,128:84 - 86.
  • 6Kang Q, Zhao Z A, You S L. Asymmetric transfer hydrogenation of β, γ-alkynyl α-imino esters by a brcnsted acid [ J ]. Org Lett,2008,10:2031 - 2034.
  • 7Rueping M, Theissmann T, Raja S, et al. Asymmetric counterion pair catalysis: An enantioselective brcnsted acid-catalyzed protonation [ J ]. Adv Synth Catal, 2008, 350 : 1001 - 1006.
  • 8Metallinos C, Barrett F B, Xu S F. Bronsted acid catalyzed asymmetric reduction of 2- and 2,9-substituted 1, lO-phenanthrolines [ J ]. Synlett ,2008:720 - 724.
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同被引文献22

  • 1S Schenker, A Zamfir, M Freund, S B Tsogoeva. Developments in Chiral Binaphthyl - Derived Bronsted/Lewis Acids and Hydrogen - Bond - Donor Organocatalysis[ J ]. Eur. J. Org. Chem. , 2011 ( 12 ) : 2 209 -2 222.
  • 2A Zamfir, S Schenker, M Freund, S B Tsogoeva. Chiral BINOL- De- rived Phosphoric Acids: Privileged Brcnsted Acid Organocatalysts for C - C Bond Formation Reactions[ J]. Org. Biomol. Chem. , 2010 (8) : 5 262 -5 276.
  • 3Q Kang, Z A Zhao, S L You. Highly Enantioselective Friedel - Crafts Reaction of Indoles with Imines by a Chiral Phosphoric Acid [ J ]. J. Am. Chem. Soc. , 2007, 129:1 484- 1 485.
  • 4Q Kang, X J Zheng, S L You. Highly Enantioselective Friedel - Crafts Reaction of 4,7 -Dihydroindoles with lmines by Chiral Phosphoric Acids: Facile Access to 2 - Indolyl Methanamine Derivatives [ J ]. Chem. Eur. J. , 2008, 14:3 539 -3 542.
  • 5Q Kang, Z A Zhao, S L You. Enantieselective Synthesis of (3 -In- dolyl) Glycine Derivatives via Asymmetric Friedel -Crafts Reaction Be- tween lndoles and Glyoxylate Imines[ J ]. Tetrahedron, 2009, 65:1 603 -1 607.
  • 6Y F Sheng, G Q Li, Q Kang, et al. Asymmetric Friedel - Crafts Reac- tion of 4,7 -Dihydroindoles with Nitroolefins by Chiral Bronsted Acids under Low Catalyst Loading[J]. Chem. Eur. J. , 2009, 15:3 351 - 3 354.
  • 7F L Sun, M Zeng, Q Gu, S L You. Enantioselective Synthesis of Flu- orene Derivatives by Chiral Phosphoric Acid Catalyzed Tandem Double Friedel-Crafts Reaction. Chem. Eur. J. , 2009, 15:8 709-8 712.
  • 8C Zheng, Y F Sheng, Y X Li, S L You. A Theoretical Investigation into Chiral Phosphoric Acid - Catalyzed Asymmetric Friedel - Crafts Reac- tions of Nitroolefins and 4,7 - Dihydroindoles: Reactivity and Enanfios- eiectivity [ J ]. Tetrahedron, 2010, 66:2 875 - 2 880.
  • 9F L Sun, X J Zheng, Q Gu, et al. Enantioselective Synthesis of Un- symmetrical Triarylmethanes by Chiral Bronsted Acids [ J ]. Eur. J. Org. Chem. , 2010:47-50.
  • 10G W Zhang, L Wang, J Nie, J A Ma. Chiral Bronsted Acid Mediated Enantioselective Organocatalytic Three - Component Reaction for the Construction of Trifluoremethyl Containing Molecules[ J]. Adv. Synth. Catal. , 2008, 350:1 457-1 463.

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合成化学
2009年 第3期

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