REVIEW

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).

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.

Cite this article

Chen Wenkun , Yang Dingqiao . Progress in Lanthanide Metals Catalyzed Asymmetric Cycloaddition Reactions[J]. Chinese Journal of Organic Chemistry, 2016 , 36(9) : 2075 -2090 . DOI: 10.6023/cjoc201604005

References

[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.

Outlines

/