将金鸡纳生物碱衍生物用于催化蒽酮和β-硝基芳基乙烯的不对称Michael加成反应.考察了溶剂、温度及催化剂用量对反应催化性能的影响.结果表明,最佳条件为5%(摩尔分数)催化剂1b、甲苯为溶剂、0℃反应,得到了91% ~99%的化学产率和最高达95% ee的对映体选择性.
参考文献
[1] | Perlmutter P.Conjugate Addition Reactions in Organic Synthesis[M].Pergamon,Oxford,1992.,1992. |
[2] | 应安国,武承林,付永前,任世斌,梁华定.有机小分子不对称催化Michael加成的研究进展[J].有机化学,2012(09):1587-1604. |
[3] | 李宁,郗国宏,吴秋华,刘伟华,马晶军,王春.有机催化不对称Michael加成反应[J].有机化学,2009(07):1018-1038. |
[4] | Krishna P R,Sreeshailam A,Srinivas R.Recent Advances and Applications in Asymmetric aza-Michael Addition Chemistry[J].Tetrahedron,2009,65 (47):9657-9672.,2009. |
[5] | Tsogoeva S B.Recent Advances in Asymmetric Organocatalytic 1,4-Conjugate Additions[J].Eur J Org Chem,2007,2007 (11):1701-1716.,2007. |
[6] | Tan B,Zeng X-F,Lu Y-P,et al.Rational Design of Organocatalyst:Highly Stereoselective Michael Addition of Cyclic Ketones to Nitroolefins[J].Org Lett,2009,11 (9):1927-1930.,2009. |
[7] | Sulzer-Mosse S,Alexakis A.Chiral Amines as Organocatalysts for Asymmetric Conjugate Addition to Nitroolefins and Vinylsulfones via Enamine Activation[J].Chem Commun,2007:,3123-3135.,2007. |
[8] | Ballini R,Bosica G,Fiorini D,et al.Conjugate Additions of Nitroalkanes to Electron-Poor Alkenes:Recent Results[J].Chem Rev,2005,105(3):933-972.,2005. |
[9] | Yang W,Jia Y,Du D M.Squaramide-Catalyzed Enantioselective Michael Addition of Malononitrile to Chalcones[J].Org Biomol Chem,2012,10(2):332-338.,2012. |
[10] | Huang H,Jacobsen E N.Highly Enantioselective Direct Conjugate Addition of Ketones to Nitroalkenes Promoted by a Chiral Primary Amine-Thiourea Catalyst[J].J Am Chem Soc,2006,128(22):7170-7171.,2006. |
[11] | Okino T,Hoashi Y,Takemoto Y.Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts[J].J Am Chem Soc,2003,125(42):12672-12673.,2003. |
[12] | Shen J,Nguyen T T,Goh Y P,et al.Chiral Bicyclic Guanidine-Catalyzed Enantioselective Reactions of Anthrones[J].J Am Chem Soc,2006,128(42):13692-13693.,2006. |
[13] | Alba A N,Bravo N,Moyano A,et al.Enantioselective Addition of Anthrones to α,α-Unsaturated Aldehydes[J].Tetrahedron Lett,2009,50 (25):3067-3069.,2009. |
[14] | Shi M,Lei Z Y,Zhao M X,et al.A highly Efficient Asymmetric Michael Addition of Anthrone to Nitroalkenes with Cinchona Organocatalysts[J].Tetrahedron Lett,2007,48(33):5743-5746.,2007. |
[15] | 何天雄,伍新燕.蒽酮与β-硝基苯乙烯的不对称Michael加成反应[J].有机化学,2010(09):1400-1404. |
[16] | Denmark S E,Marcin L R.A General Method for the Preparation of 2,2-Disubstituted 1-Nitroalkenes[J].J Org Chem,1993,58(15):3850-3856.,1993. |
[17] | Zhang T Y,He W,Zhao X Y,et al.Asymmetric Oxaziridination Catalyzed by Cinchona Alkaloid Derivatives Containing Sulfide[J].Tetrahedron,2013,69(35):7416-7422.,2013. |
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