综述与进展

镧系金属催化不对称环加成反应研究进展

  • 陈文坤 ,
  • 杨定乔
展开
  • 华南师范大学化学与环境学院 教育部环境理论化学重点实验室 广州 510006

收稿日期: 2016-04-03

  修回日期: 2016-04-29

  网络出版日期: 2016-05-19

基金资助

国家自然科学基金(Nos.21172081,21372090)、广东省自然科学基金重点(No.S2013020013091)和广州市科技计划(No.156300018)资助项目.

Progress in Lanthanide Metals Catalyzed Asymmetric Cycloaddition Reactions

  • Chen Wenkun ,
  • Yang Dingqiao
Expand
  • Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2016-04-03

  Revised date: 2016-04-29

  Online published: 2016-05-19

Supported by

Project supported by the National Natural Science Foundation of China (Nos.21172081, 21372090), the Natural Science Foundation of Guangdong Province (No.S2013020013091) and the City of Guangzhou Science and Technology Plan Projects (No.156300018).

摘要

综述了近年来镧系金属催化不对称环加成反应的研究进展,主要包括[4+2]、[3+2]、[2+2]和[2+1]不对称环加成反应.并对部分环加成反应可能的机理进行了讨论.

本文引用格式

陈文坤 , 杨定乔 . 镧系金属催化不对称环加成反应研究进展[J]. 有机化学, 2016 , 36(9) : 2075 -2090 . DOI: 10.6023/cjoc201604005

Abstract

The recent progress in lanthanide metals catalyzed asymmetric cycloaddition reactions is reviewed, mainly including[4+2],[3+2],[2+2] and[2+1] asymmetric cycloaddition reactions. Moreover, the possible mechanisms of some parts of reactions are also discussed.

参考文献

[1] Qian,C.-T.;Wang,C.-H.;Chen,Y.-F.Acta Chim.Sinica 2014,72,883(in Chinese). (钱长涛,王春红,陈耀峰,化学学报,2014,72,883.)
[2] Qian,C.-T.;Du,C.-P.Organolanthanide Chemistry,Chemical Industry Press,Beijing,2004(in Chinese). (钱长涛,杜灿屏,稀土金属有机化学,化学工业出版社,北京,2004.)
[3] Averill,D.J.;Allen,M.J.Catal.Sci.Technol.2014,4,4129.
[4] Kumagai,N.;Shibasaki,M.Angew.Chem.,Int.Ed.2013,52,223.
[5] Edelmann,F.T.Coord.Chem.Rev.2014,261,73.
[6] Ward,B.D.;Gade,L.H.Chem.Commun.2012,48,10587.
[7] Jia,Y.;Fan,M.;Chen,H.-N.;Miao,Y.-T.;Xing,L.;Jiang,B.-H.;Cheng,Q.-F.;Liu,D.-W.;Bao,W.-K.;Qian,B.;Wang,J.-L.;Xing,X.-D.;Tan,H.-P.;Ling,Z.-H.;Chen,Y.J.Colloid Interface Sci.2015,458,293.
[8] Kotha,S.;Deodhar,D.;Khedkar,P.Org.Biomol.Chem.2014,12,9054.
[9] Juhl,M.;Tanner,D.Chem.Soc.Rev.2009,38,2983.
[10] Healy,A.R.;Westwood,N.J.Org.Biomol.Chem.2015,13,10527.
[11] Smith,L.K.;Baxendale,L.R.Org.Biomol.Chem.2015,13,9907.
[12] Takao,K.I.;Munakata,R.;Tadano,K.I.Chem.Rev.2005,105,4779.
[13] Bednarski,M.;Damishotsky,S.J.Am.Chem.Soc.1983,105,3716.
[14] Bednarski,M.;Maring,C.;Damishotsky,S.Tetrahedron Lett.1983,24,3451.
[15] Luo,R.-S.;Yang,D.-Q.Chin.J.Org.Chem.2007,27,958(in Chinese). (罗人仕,杨定乔,有机化学,2007,27,958.)
[16] Hu,P.;Long,Y.-H.;Wang,H.;Mo,H.-H.Chin.J.Org.Chem.2008,28,1181(in Chinese). (胡萍,龙玉华,王辉,莫海洪,杨定乔,有机化学,2008,28,1181.)
[17] Bian,H.-X.;Yang,D.-Q.Chin.J.Org.Chem.2010,30,506(in Chinese). (边红旭,杨定乔,有机化学,2010,30,506.)
[18] Duan,Z.-B.;Long,Y.-H.;Yang,D.-Q.Chin.J.Org.Chem.2010,30,368(in Chinese). (段泽斌,龙玉华,杨定乔,有机化学,2010,30,368.)
[19] Zeng,Z.-Y.;Yang,D.-Q.Chin.J.Org.Chem.2013,33,2131(in Chinese). (曾中一,杨定乔,有机化学,2013,33,2131.)
[20] Cheng,G.;Yang,D.-Q.Chin.J.Org.Chem.2015,35,2023(in Chinese). (程果,杨定乔,有机化学,2015,35,2023.)
[21] (a) Furuta,K.;Miwa,Y.;Iwanaga,K.;Yamamoto,H.J.Am.Chem.Soc.1988,110,6254. (b) Chapuis,C.;Jurczak,J.Helv.Chim.Acta 1987,70,436. (c) Narasaka,K.;Inoue,M.;Okada,N.Chem.Lett.1986,1109. (d) Maruoka,K.;Itoh,T.;Shirasaka,T.;Yamamoto,H.J.Am.Chem.Soc.1988,110,310. (e) Oppolzer,W.Angew.Chem.,Int.Ed.1984,23,876.
[22] Corey,E.J.Angew.Chem.,Int.Ed.2002,41,1650.
[23] (a) Diels,O.;Alder,K.Ann.Chem.1926,450,237. (b) Diels,O.;Alder,K.Ann.Chem.1927,460,98.
[24] Desimoni,G.;Faita,G.;Guala,M.;Laurenti,A.Eur.J.Org.Chem.2004,14,3057.
[25] Desimoni,G.;Faita,G.;Guala,M.;Laurenti,A.;Mella,M.Chem.Eur.J.2005,11,3816.
[26] Desimoni,G.;Faita,G.;Guala,M.;Piccinini,F.;Toscanini,M.Eur.J.Org.Chem.2007,9,1529.
[27] Fukuzawa,S.I.;Yahara,Y.;Kamiyama,A.;Hara,M.;Kikuchi,S.Org.Lett.2005,7,5809.
[28] Li,C.;Wang,H.CN 101116828,2006[Chem.Abstr.2008,148,308326].
[29] Sudo,Y.;Shirasaki,D.;Harada,S.;Nishida,A.J.Am.Chem.Soc.2008,130,12588.
[30] Harada,S.;Toudou,N.;Hiraoka,S.;Nishida,A.Tetrahedron Lett.2009,50,5652.
[31] Hiraoka,S.;Harada,S.;Nishida,A.J.Org.Chem.2010,75,3871.
[32] Harada,S.;Morikawa,T.;Nishida,A.Org.Lett.2013,15,5314.
[33] Mikami,K.;Kotera,O.;Motoyama,Y.;Sakaguchi,H.Synlett 1995,975.
[34] (a) Kobayashi,S.;Sugiura,M.;Kitagawa,H.;Lam,W.W.Chem.Rev.2002,102,2227. (b) Kobayashi,S.In Topics in Organometallic Chemistry,Vol.2,Ed.:Beller,M.,Springer,Berlin,1999,p.77. (c) Shibasaki,M.;Yamada,K.;Yoshikawa,N.In Lewis Acids in Organic Synthesis,Ed.:Yamamoto,H.,Wiley,Weinheim,2000,Chapter 20.2. (d) Aplander,K.;Ding,R.;Lindstrom,U.M.;Wennerberg,J.;Schultz,S.Angew.Chem.,Int.Ed.2007,46,4543.
[35] Qian,C.-T.;Wang,L.-C.Tetrahedron Lett.2000,41,2203.
[36] Furuno,H.;Kambara,T.;Tanaka,Y.;Hanamoto,T.;Kagawa,T.;Inanaga,J.Tetrahedron Lett.2003,44,6129.
[37] Furuno,H.;Hanamoto,T.;Sugimoto,Y.;Inanaga,J.Org.Lett.2000,2,49.
[38] Tiseni,P.S.;Peters,R.Org.Lett.2008,10,2019.
[39] Zhu,Y.;Xie,M.-S.;Dong,S.;Zhao,X.-H.;Lin,L.-L.;Liu,X.-H.;Feng,X.-M.Chem.Eur.J.2011,17,8202.
[40] Xu,Z.-H.;Liu,L.;Wheeler,K.;Wang,H.Angew.Chem.,Int.Ed.2011,50,3484.
[41] Luan,Y.;Barbato,K.S.;Moquist,P.N.;Kodama,T.;Schaus,S.E.J.Am.Chem.Soc.2015,137,3233.
[42] (a) Ishitani,H.;Kobayashi,S.Tetrahedron Lett.1996,37,7357. (b) Kobayashi,S.;Nagayama,S.J.Am.Chem.Soc.1996,118,8977.
[43] Chen,Z.-L.;Lin,L.-L.;Chen,D.-H.;Li,J.-T.;Liu,X.-H.;Feng,X,-M.Tetrahedron Lett.2010,51,3088.
[44] Jørgensen,K.A.Angew.Chem.,Int.Ed.2000,39,3558.
[45] Deng,Y.M.;Karunaratne,C.V.;Csatary,E.;Tierney,D.L.;Wheeler,K.;Wang,H.J.Org.Chem.2015,80,7984.
[46] Hrdina,R.;Guenee,L.;Moraleda,D.;Lacour,J.Organometallics 2013,32,473.
[47] Xiao,Q.;Young,K.;Zakarian,A.Org.Lett.2013,15,3314.
[48] Young,K.;Xiao,Q.;Zakarian,A.Eur.J.Org.Chem.2013,11,2337.
[49] Gothelf,K.V.;Jorgensen,K.A.Chem.Rev.1998,98,863.
[50] Frederickson,M.Tetrahedron 1997,53,403.
[51] Hashimoto,T.;Maruoka,K.J.Am.Chem.Soc.2015,115,9653.
[52] Yamamoto,H.;Hayashi,S.;Kubo,M.;Harada,M.;Hasegawa,M.;Noguchi,M.;Sumimoto,M.;Hori,K.Eur.J.Org.Chem.2007,17,2859.
[53] Gucma,M.;Gobiewski,W.M.J.Heterocycl.Chem.2008,45,241.
[54] Gobiewski,W.M.;Gucma,M.J.Heterocycl.Chem.2008,45,1687.
[55] Gucma,M.;Gobiewski,W.M.Catal.Sci.Technol.2011,1,1354.
[56] Suga,H.;Inoue,K.;Inoue,S.;Kakehi,A.;Shiro,M.J.Org.Chem.2005,70,47.
[57] Padwa,A.;Weingarten,M.D.Chem.Rev.1996,96,223.
[58] Padwa,A.;Hornbuckle,S.F.Chem.Rev.1991,91,263.
[59] Suga,H.;Shimoto,D.;Higuchi,S.;Ohtsuka,M.;Arikawa,T.;Tsuchida,T.;Kakehi,A.;Baba,T.Org.Lett.2007,9,4359.
[60] Suga,H.;Higuchi,S.;Ohtsuka,M.;Ishimoto,D.;Arikawa,T.;Hashimoto,Y.;Misawa,S.;Tsuchida,T.;Kakehi,A.;Baba,T.Tetrahedron 2010,66,3037.
[61] Suga,H.;Hashimoto,Y.;Yasumura,S.;Takezawa,R.;Itoh,K.;Kakehi,A.J.Org.Chem.2013,78,10840.
[62] Chen,W.-L.;Lin,L.-L.;Cai,Y.-F.;Xia,Y.;Cao,W.-D.;Liu,X.-H.;Feng,X.-M.Chem.Commun.2014,50,2161.
[63] Kobayashi,S.;Kawamura,M.J.Am.Chem.Soc.1998,120,5840.
[64] Evans,D.A.;Song,H.-J.;Fandrick,K.R.Org.Lett.2006,8,3351.
[65] Barros,M.T.;Faísca Phillips,A.M.Tetrahedron:Asymmetry 2010,21,2746.
[66] Tonoi,T.;Mikami,K.Tetrahedron Lett.2005,46,6355.
[67] Narasaka,K.;Hayashi,Y.;Shimadzu,H.;Niihata,S.J.Am.Chem.Soc.1992,114,8869.
[68] Fan,B.-M.;Li,X.-J.;Peng,F.-Z.;Zhang,H.-B.;Chan,A.C.S.;Shao,Z.H.Org.Lett.2010,12,304.
[69] Aggarwal,V.K.;Belfield,A.J.Org.Lett.2003,5,5075.
[70] France,S.;Wack,H.;Hafez,A.M.;Taggi,A.E.;Witsil,D.R.;Lectka,T.Org.Lett.2002,4,1603.
[71] Calter,M.A.;Tretyak,O.A.;Flaschenriem,C.Org.Lett.2005,7,1809.
[72] Huang,Y.-Z.;Calter,M.A.Tetrahedron Lett.2007,48,1657.
[73] Kakei,H.;Sone,T.;Sohtome,Y.;Matsunaga,S.;Shibasaki,M.J.Am.Chem.Soc.2007,129,13410.

文章导航

/