一个金鸡纳碱衍生物的合成以及对靛红和硝基甲烷Henry反应的催化
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摘要
用S-联二萘酚通过Mitsunobu反应与奎宁结合,制备1个新型金鸡纳碱催化剂。新催化剂结构:用质谱、核磁共振氢谱确定了目标化合物的结构,总收率达15%。将该催化剂用于靛红和硝基甲烷Henry反应,获得ee值9%,产率99%的加成产物。
A new type of quinine catalyst was prepared via(S)-(-)-1,1'-Bi(2-naphthol) and quinine by Mitsunobu reaction. The structure of new catalyst structuret compound was determined by mass spectrometry, nuclear magnetic resonance hydrogen spectrum, and the total yield was 15%. The catalyst was used for the Henry reaction of isatin and nitromethane, obtaining 9% of the ee value and 99% of the product yield.
A new type of quinine catalyst was prepared via(S)-(-)-1,1'-Bi(2-naphthol) and quinine by Mitsunobu reaction. The structure of new catalyst structuret compound was determined by mass spectrometry, nuclear magnetic resonance hydrogen spectrum, and the total yield was 15%. The catalyst was used for the Henry reaction of isatin and nitromethane, obtaining 9% of the ee value and 99% of the product yield.
引文
[1]Luo S,Mi M,Zhang L,et al.Asymmetric Organoeatalytic Henry Reaction[J].Angew.Chem.Int.Ed.2006,118(6):929-931.
[2]Wang W,Liu L,Xue F,et al.Catalytie Enantioselective Henry Reactions of Isatins:Application in the Concise Synthesis of(S)-(-)-Spirobrassinin.Chem[J].Eur.J.2011,17(28):7791-7795.
[3]Wang W,Liu L,Wu D,et al.Synthesis of Highly Functionalized Chiral 3,3'-Disubstituted Oxindoles via an Organocatalytic Enantioselective Michael Addition of Nitroalkanes to Indolylidene-cyanoacetic Acetates[J].Org.Lett.2005,8(12):91-96.
[4]Swamy K C K,Kumar N N,Balaraman E,et al.Mitsunobu and related reactions:advances and applications[J].Chem.Rev.2009,109(6):2551-2651.
[2]Wang W,Liu L,Xue F,et al.Catalytie Enantioselective Henry Reactions of Isatins:Application in the Concise Synthesis of(S)-(-)-Spirobrassinin.Chem[J].Eur.J.2011,17(28):7791-7795.
[3]Wang W,Liu L,Wu D,et al.Synthesis of Highly Functionalized Chiral 3,3'-Disubstituted Oxindoles via an Organocatalytic Enantioselective Michael Addition of Nitroalkanes to Indolylidene-cyanoacetic Acetates[J].Org.Lett.2005,8(12):91-96.
[4]Swamy K C K,Kumar N N,Balaraman E,et al.Mitsunobu and related reactions:advances and applications[J].Chem.Rev.2009,109(6):2551-2651.