硫叶立德参与的Domino环化反应
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  • 英文篇名:Sulfur Ylides Participating Domino Cyclization Reaction
  • 作者:李公春 ; 王利叶 ; 黄有
  • 英文作者:Li, Gongchun;Wang, Liye;Huang, You;College of Chemistry and Chemical Engineering, Xuchang University;Research Institute of Elemento-Organic Chemistry, State Key Laboratory of Elemento-Organic Chemistry,Nankai University;
  • 关键词:硫叶立德 ; Domino环化反应 ; 合成
  • 英文关键词:sulfur ylide;;Domino cyclization reaction;;synthesis
  • 中文刊名:YJHU
  • 英文刊名:Chinese Journal of Organic Chemistry
  • 机构:许昌学院化学化工学院;南开大学元素有机化学研究所元素有机化学国家重点实验室;
  • 出版日期:2013-09-15
  • 出版单位:有机化学
  • 年:2013
  • 期:v.33;No.298
  • 语种:中文;
  • 页:YJHU201309005
  • 页数:19
  • CN:09
  • ISSN:31-1321/O6
  • 分类号:61-79
摘要
硫叶立德参与的Domino环化反应在有机合成中具有重要的意义,能够方便地从简单的原料出发,高效地构建多个化学键,合成具有结构多样性和复杂性的有机分子,硫叶立德参与的Domino环化反应被化学界广泛地关注.综述了近年来硫叶立德参与的Domino环化反应合成三元环、五元环、六元环和多元并环类化合物的研究进展.
        ulfur ylide participating domino cyclization reaction is of great importance in organic synthesis, since it can efficiently build multiple chemical bonds from simple raw material, and it can efficiently synthesize organic molecules with diversified and complicated structures. Chemists have paid extensive attentions to sulfur ylide participating domino cyclization reaction. This review presents the recent progress on the sulfur ylide participating domino cyclization reaction synthesizing derivatives of three-membered rings, five-membered rings, six-membered rings and bridge rings.
引文
[1](a)Tietze,L.F.;Brasche,G.;Gericke,K.Domino Reactions in Organic Synthesis,Wiley-VCH,Weinheim,Germany,2006.(b)Nicolaou,K.C.;Montagnon,T.;Snyder,S.A.Chem.Commun.2003,551.
    [2](a)Enders,D.;Grondal,C.;Hüttl,M.R.Angew.Chem.,Int.Ed.2007,46,1570.(b)Grondal,C.;Jeanty,M.;Enders,D.Nat.Chem.2010,2,167.(c)Guo,H.C.;Ma,J.A.Angew.Chem.,Int.Ed.2006,45,354.(d)Tietze,L.F.Chem.Rev.1996,96,115.(e)Tietze,L.F.;Beifuss,U.Angew.Chem.,Int.Ed.1993,32,131.
    [3](a)Han,X.;Ye,L.W.;Sun,X.L.Chin.J.Org.Chem.2009,29,309(in Chinese).(韩讯,叶龙武,孙秀丽,有机化学,2009,29,309.)(b)Wang,M.;Zhang,H.;Chen,J.;Wu,X.X.;Deng,H.M.;Shao,M.;Cao,W.G.Chin.J.Org.Chem.2009,29,1611(in Chinese).(王猛,张慧,陈杰,吴小余,邓红梅,邵敏,曹卫国,有机化学,2009,29,1611.)(c)Xiao Q.;Wang J.B.Acta Chim.Sinica 2007,65,1733(in Chinese).(肖卿,王剑波,化学学报,2007,65,1733.)(d)Lu,L.Q.Ph.D.Dissertation,Central China Normal University,Wuhan,2011(in Chinese).(陆良秋,博士论文,华中师范大学,武汉,2011.)(e)Zhu,B.H.Ph.D.Dissertation,Suzhou University,Suzhou,2010(in Chinese).(朱本虎,博士论文,苏州大学,苏州,2010.)
    [4]Aggarwal,V.K.;Winn,C.L.Acc.Chem.Res.2004,37,611.
    [5]Sun,X.L.;Tang,Y.Acc.Chem.Res.2008,41,937.
    [6]Lu,L.Q.;Chen,J.R.;Xiao,W.J.Acc.Chem.Res.2012,45,1278.
    [7]Johnson,A.W.;LaCount,R.B.Chem.Ind.(London)1958,1440.
    [8]Corey,E.J.;Chaykovsky,M.J.Am.Chem.Soc.1965,87,1353.
    [9](a)Johnson,C.R.;Schroeck,C.W.J.Am.Chem.Soc.1968,90,6852.(b)Johnson,C.R.;Schroeck,C.W.J.Am.Chem.Soc.1973,95,7418
    [10]Piccinini,A.;Kavanagh,S.A.;Connon,P.B.;Connon,S.J.Org.Lett.2010,12,608.
    [11]Furukawa,N.;Sugihara,Y.;Fujihara,H.J.Org.Chem.1989,54,4222.
    [12]Zanardi,J.;Leriverend,C.;Aubert,D.;Julienne,K.;Metzner,P.J.Org.Chem.2001,66,5620.
    [13]McGarrigle,E.M.;Myers,E.L.;Illa,O.;Shaw,M.A.;Riches,S.L.;Aggarwal,V.K.Chem.Rev.2007,107,5841.
    [14]Zhou,Y.G.;Hou,X.L.;Dai,L.X.;Xia,L.J.;Tang,M.H.J.Chem.Soc.,Perkin Trans.1 1999,77.
    [15]Aggarwal,V.K.;Hynd,G.;Picoul,W.;Vasse,J.L.J.Am.Chem.Soc.2002,124,9964.
    [16](a)Forbes,D.C.;Standen,M.C.;Lewis,D.L.Org.Lett.2003,5,2285.(b)Forbes,D.C.;Amin,S.R.;Bean,C.J.;Standen,M.C.J.Org.Chem.2006,71,8287.
    [17]Schulz,V.;Davoust,M.;Lemarie,M.;Lohier,J.F.;Sopkova,J.;Santos,O.;Metzner,P.;Brière,J.F.Org.Lett.2007,9,1745.
    [18]Padwa,A.;Hornbuckle,S.F.Chem.Rev.1991,91,263.
    [19]Aggarwal,V.K.;Hesham,A.R.;Li,F.;Jones,R.V.H.;Standen,M.C.H.Chem.Eur.J.1996,2,1024.
    [20]Aggarwal,V.K.;Ford,J.G.;Thompson,A.;Jones,R.V.H.;Standen,M.C.H.J.Am.Chem.Soc.1996,118,7004.
    [21]Aggarwal,V.K.;Ford,J.G.;Fonquerna,S.;Adams,H.;Jones,R.V.H.;Fieldhouse,R.J.Am.Chem.Soc.1998,120,8328.
    [22]Bellenie,B.R.;Goodman,J.M.Chem.Commun.2004,1076.
    [23]Aggarwal,V.K.;Charmant,J.;Dudin,L.;Porcelloni,M.;Richardson,J.PNAS㎜2004,101,5467.
    [24]Aggarwal,V.K.;Alonso,E.;Hynd,G.;Lydon,K.M.;Palmer,M.J.;orcelloni,M.;Studley,J.R.Angew.Chem.,Int.Ed.2001,40,1430.
    [25]Aggarwal,V.K.;Harvey,J.N.;Richardson,J.J.Am.Chem.Soc.2002,124,5747.
    [26]Aggarwal,V.K.;Bae,I.;Lee,H.Y.;Richardson,J.;Williams,D.T.Angew.Chem.,Int.Ed.2003,42,3274.
    [27]Li,A.H.;Dai,L.X.;Hou,X.L.;Chen,M.B.J.Org.Chem.1996,61,4641.
    [28]Li,A.H.;Dai,L.X.;Hou,X.L.J.Chem.Soc.,Perkin Trans.11996,867.
    [29]Wang,D.K.;Dai,L.X.;Hou,X.L.Chem.Commun.1997,1231.
    [30]Li,A.H.;Zhou,Y.G.;Dai,L.X.;Hou,X.L.;Xia,L.J.;Lin,L.Angew.Chem.,Int.Ed.1997,36,1317.
    [31]Saito,T.;Sakairi,M.;Akiba,D.Tetrahedron Lett.2001,42,5451.
    [32]Robiette,R.J.Org.Chem.2006,71,2726.
    [33]Aggarwal,V.K.;Christopher,M.F.;O’Brien,J.;Thompson,A.;Jones,R.V.H.;Fieldhouse,R.J.Chem.Soc.,Perkin Trans.12001,1635.
    [34]Yang,X.F.;Zhang,M.J.;Hou,X.L.;Dai,L.X.J.Org.Chem.2002,67,8097.
    [35]Morton,D.;Pearson,D.;Field,R.A.;Stockman,R.A.Org.Lett.2004,6,2377.
    [36]Morton,D.;Pearson,D.;Field,R.A.;Stockman,R.A.Chem.Commun.2006,1833.
    [37](a)Patai,S.;Rappoport,Z.The Chemistry of the Cyclopropyl Group,Wiley and Sons,New York,1987.(b)Krief,A.In Small Ring Compounds in Organic Synthesis,VI,Eds.:de Meijere,A.;Schaumann,E.,Springer,Berlin,2000,207,1.
    [38](a)Donaldson W.A.Tetrahedron 2001,57,8589.(b)Lebel,H.;Marcoux,J.F.;Molinaro,C.;Charette,A.B.Chem.Rev.2003,103,977.
    [39]Cyrils,F.;Apopoet,T.D.H.J.Org.Chem.1973,38,2806.
    [40]Oswald,M.F.;Raw,S.A.;Taylor,R.J.K.Org.Lett.2004,6,3997.
    [41]Oswald,M.F.;Raw,S.A.;Taylor,R.J.K.Chem.Commun.2005,2253.
    [42]Johnson,C.R.;Schroeck,C.W.J.Am.Chem.Soc.1968,90,6852.
    [43](a)Solladie-Cavallo,A.;Diepvohuule,A.;Isarno,T.Angew.Chem.,Int.Ed.1998,37,1689.(b)Solladie-Cavallo,A.Enantiomer 1999,4,173.
    [44]Kunz,R.K.;Macmillan,D.W.C.J.Am.Chem.Soc.2005,127,3240.
    [45]Ye,S.;Huang,Z.Z.;Xia,C.A.;Tang,Y.;Dai,L.X.J.Am.Chem.Soc.2002,124,2432.
    [46]Deng,X.M.;Cai,P.;Ye,S.;Sun,X.L.;Tang,Y.;Wu,Y.D.;Dai,L.X.J.Am.Chem.Soc.2006,128,9730.
    [47]Kumaran,G.;KulKarni,G.H.Synthesis 1995,1545.
    [48]Jiang,Y.;Ma,D.Tetrahderon:Asymmetry 2002,13,1033.
    [49]Deng,W.P.;Li,A.H.;Dai,L.X.;Hou,X.L.Tetrahderon 2000,56,2967
    [50]Schomaker,J.M.;Pulgam,V.R.;Borhan,B.J.Am.Chem.Soc.2004,126,13600.
    [51]Gais,H.J.;Reddy,L.R.;Babu,G.S.J.Am.Chem.Soc.2004,126,4859.
    [52]Bernard,A.M.;Frongia,A.;Piras,P.P.;Secci,F.;Spiga,M.Org.Lett.2005,7,4565.
    [53]Zheng,J.C.;Zhu,C.Y.;Sun,X.L.;Tang,Y.;Dai,L.X.,J.Org.Chem.2008,73,6909.
    [54]Li,A.H.;Dai,L.X.;Hou,X.L.;Chen,M.B.J.Org.Chem.1996,61,4641.
    [55]Tiwari,S.K.;Gais,H.J.;Lindenmaier,A.;Babu,G.S.;Raabe,G.;Reddy,L.R.;Kohler,F.;Gunter,M.;Koep,S.;Iska,V.B.R.J.Am.Chem.Soc.2006,128,7360.
    [56]Schomaker,J.M.;Bhattacharjee,S.;Yan,J.;Borhan,B.J.Am.Chem.Soc.2007,129,1996.
    [57]Hodgson,D.M.;Fleming,M.J.;Xu,Z.Q.;Stanway,S.J.Chem.Commun.2006,3226.
    [58]Kim,K.H.;Jimenez,L.S.Tetrahedron:Asymmetry 2001,12,999.
    [59]Kokotos,C.G.;Aggarwal,V.K.Chem.Commun.2006,2156.
    [60]Unthank,M.G.;Hussain,N.;Aggarwal,V.K.Angew.Chem.,Int.Ed.2006,45,7066.
    [61]Lu,L.Q.;Zhang,J.J.;Li,F.;Cheng,Y.;An,J.;Xiao,W.J.Angew.Chem.,Int.Ed.2010,49,4597.
    [62]Zhu,C.Y.;Sun,X.L.;Deng,X.M.;Zheng,J.C.;Tang,Y.Tetrahedron 2008,64,5583.
    [63]Lu,L.Q.;Cao,Y.J.;Liu,X.P.;An,J.;Xiao,W.J.J.Am.Chem.Soc.2008,130,6946.
    [64]Matsuo,J.;Yamanaka,H.;Kawana,A.;Mukaiyama,T.Chem.Lett.2003,32,392.
    [65]Unthank,M.G.;Hussain,N.;Aggarwal,V.K.Angew.Chem.,Int.Ed.2006,45,7006.
    [66]Yar,M.;McGarrigle,E.;Aggarwal,V.K.Angew.Chem.,Int.Ed.2008,47,3784.
    [67]Neff,J.R.;Gruetzmacher,R.R.;Nordlander,J.E.J.Org.Chem.1974,39,3814.
    [68]Wang,Q.G.;Deng,X.M.;Zhu,B.H.;Ye,L.W.;Tang Y.J.Am.Chem.Soc.2008,130,5408.
    [69]Zhu,B.H.;Zhou,R.;Zheng,J.C.;Shen,Q.;Tang,Y.J.Org.Chem.2010,75,3454.
    [70]Aggarwal,V.K.;Grange,E.Chem.Eur.J.2006,12,568.
    [71]Chen,Z.;Zhang,J.Chem.Asian J.2009,4,1527.
    [72]Ye,L.W.;Sun,X.L.;Zhu,C.Y.;Tang,Y.Org.Lett.2006,8,3853.
    [73]Zhu,B.H.;Zheng,J.C.;Yu,C.B.;Sun,X.L.;Zhou,Y.G.;Shen,Q.;Tang,Y.Org.Lett.2010,12,504.
    [74]An,J.;Chang,N.J.;Song,L.D.;Chen,J.R.;Xiao,W.J.Chem.Commumn.2011,47,1869.
    [75]Lu,L.Q.;Ming,Z.H.;An,J.;Li,C.;Chen,J.R.;Xiao,W.J.J.Org.Chem.2012,77,1072.
    [76]Yang,Q.Q.;Xiao,C.;Lu,L.Q.;An,J.;Tan,F.;Li,B.J.;Xiao,W.J.Angew.Chem.,Int.Ed.2012,51,9137.
    [77]Yamashita,M.;Okuyama,K.;Kawajiri,T.;Ohta,S.Tetrahedron2002,58,1497.
    [78]Yamashita,M.;Inaba,T.;Nagahaxna,M.;Ohta,S.Org.Biomol.Chem.2005,3,2296.
    [79]Yadav,N.D.;Yamashita,M.;Nagahama,M.;Ohta,S.Tetrahedron Lett.2008,49,162.
    [80]Xie,P.Z.;Wang,L.Y.;Yang,L.H.;Li,E.Q.;Ma,J.Z.;Huang,Y.;Chen,R.Y.J.Org.Chem.2011,76,7699.
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