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Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction 被引量:1

Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction
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摘要 In the past decade, the asymmetric Morita-Baylis-Hillman (MBH)/aza-Morita-Baylis-Hillman (aza-MBH) reaction has attracted great attention because it leads to the formation of densely functionalized products in a catalytic and atom-economic way. The MBH/aza-MBH adducts can be further applied in a wide variety of organic synthesis, such as peptide synthesis and heterocyclic compounds synthesis. After a lot of attempts to improve the enantioselectivity, many types of chiral organocatalysts have been identified as highly enantioselective organocatalysts in MBH/aza-MBH reaction. Especially, certain "privileged chiral catalysts" are highly enantioselective in MBH/aza-MBH reaction, which are designed and developed through introducing bi-/multi-functional groups on the so-called "privileged structures" such as cinchona alkaloids, BINAP/BINOL. This review summarizes the exciting advances about the design and development of chiral catalysts derived from "privileged structures" and their applications in asymmetric MBH/aza-MBH reaction. In the past decade, the asymmetric Morita-Baylis-Hillman (MBH)/aza-Morita-Baylis-Hillman (aza-MBH) reaction has attracted great attention because it leads to the formation of densely functionalized products in a catalytic and atom-economic way. The MBH/aza-MBH adducts can be further applied in a wide variety of organic synthesis, such as peptide synthesis and heterocyclic compounds synthesis. After a lot of attempts to improve the enantioselectivity, many types of chiral organocatalysts have been identified as highly enantioselective organocatalysts in MBH/aza-MBH reaction. Especially, certain "privileged chiral catalysts" are highly enantioselective in MBH/aza-MBH reaction, which are designed and developed through introducing hi-/multi-functional groups on the so-called "privileged structures" such as cinchona alkaloids, BINAP/BINOL. This review summarizes the exciting advances about the design and development of chiral catalysts derived from "privileged structures" and their applications in asymmetric MBH/aza-MBH reaction.
出处 《Chinese Science Bulletin》 SCIE EI CAS 2010年第17期1699-1711,共13页
基金 supported by Shanghai Municipal Committee of Science and Technology (06XD14005 and 08dj1400100-2) National Basic Research Program of China (2009CB825300) the National Natural Science Foundation of China (20872162, 20672127, 20821002 and 20732008)
关键词 手性催化剂 选择性反应 不对称 氮杂 特权 对映选择性 有机催化剂 有机合成 Morita-Baylis-Hfllman/aza-Morita-Baylis-Hillman reaction, privileged chiral catalysts, organocatalysts, chiral amines, chiral phosphines
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参考文献70

  • 1Morita K, Suzuki Z, Hirose H. A tertiary phosphine-catalyzed reaction of acrylic compounds with aldehydes. Bull Chem Soc Jpn, 1968, 41:2815.
  • 2Baylis A B, Hillman M E D. US Pantent 3 743 669, 1972.
  • 3Drewes S E, Roos G H P. Synthetic potential of the tertiaryamine-catalysed reaction of activated vinyl carbanions with aldehydes. Tetrahedron, 1988, 44:4653-4670.
  • 4Basavaiah D, Rao P D, Hyma R S. The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction. Tetrahedron, 1996, 52: 8001-8062.
  • 5Ciganek E. Organic reactions. New York: John Wiley & Sons. Inc. 1997, 51:201-210.
  • 6Basavaiah D, Rao A J, Satyanarayana T. Recent advances in the Baylis- Hillman reaction and applications. Chem Rev, 2003, 103:811-891.
  • 7Basavaiah D, Rao K V, Reddy R J. The Baylis-Hillman reaction: A novel source of attraction, opportunities, and challenges in synthetic chemistry. Chem Soc Rev, 2007, 36:1581-1588.
  • 8Singh V, Batra S. Advances in the Baylis-Hillman reaction-assisted synthesis of cyclic frameworks. Tetrahedron, 2008, 64:4511-4574.
  • 9Perlmutter P, Teo C C. A simple synthesis of 2-methylidene-3- aminopropanoates. Tetrahedron Lett, 1984, 25:5951-5952.
  • 10Tang X, Zhang B, He Z, et al. 1,3,5-Triaza-7-phosphaadamantane: A practical and versatile nucleophilic phosphine organocatalyst. Adv Synth Catal, 2007, 349:2007-2017.

同被引文献4

  • 1Iwabuchi Y,Nakatani M,Yokoyama N,et al.ChiralAmine-Catalyzed Asymmetric Baylis-Hillman Re-action:A Reliable Route to Highly EnantiomericallyEnriched(α-Methylene-β-hydroxy)esters. Journal of the American Chemical Society . 1999
  • 2Rafel S,Leahy J W.An Unexpected Rate Accelerations Practical Improvements in the Baylis-Hillman Reaction. Journal of Organic Chemistry . 1997
  • 3Iwabuchi Y,Hatakeyama S.Recent progress in the Morita-Baylis-Hillman reactions. J. Synth. Org. Chem. Jpn. ( Yuki Gosei Kagaku Kyokaishi . 2002
  • 4Barrett, A. G. M.,Cook, A. S.,Kamimura, A.Asymmetric Baylis-Hillman Reactions: Catalysis Using a Chiral Pyrrolizidine Base. Chemical Communications . 1998

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