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化学进展 2007, Vol. 19 Issue (06): 902-910 前一篇   后一篇

• 综述与评论 •

手性pybox-金属络合物及其在不对称催化反应中的应用

钟丽琴；唐瑞仁*；杨青   

  1. 中南大学化学化工学院 长沙 410083
  • 收稿日期:2006-07-31 修回日期:2006-08-30 出版日期:2007-06-24 发布日期:2007-06-24
  • 通讯作者: 唐瑞仁
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导出 被引次数 ( 11 | 1 )

The Chiral Metal Complexes of Pyridine-2,6-bis(oxazolino) and Their Applications in Catalytic Asymmetric Reactions

zhong Liqin；Tang Ruiren*；Yang Qing   

  1. College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China
  • Received:2006-07-31 Revised:2006-08-30 Online:2007-06-24 Published:2007-06-24
具有C2对称性的双噁唑啉型吡啶(pybox)是一类有效的手性配体，能与许多金属离子配位，其手性催化性能已得到越来越多的关注。本文综述了手性配体pybox和pybox-金属络合物的合成方法，特别是近年来pybox-金属络合物在不对称催化反应如不对称环丙烷化反应、不对称Diels-Alder反应、1,3-偶极环加成反应、不对称aldol反应等中应用的最新进展。
关键词： 二噁唑啉基吡啶, 手性催化剂, 不对称催化反应, 金属络合物
Pyridine-2,6-bis-(oxazolino)（pybox）which has C2-symmetry is a kind of effective chiral ligands, it can coordinate with many metal cations. Asymmetric catalysis with chiral complexes has received considerable attention in recent years. In this paper the preparation of chiral pybox ligands and their metal complexes are reviewed, especially the application of chiral pybox-metal complexes in catalytic asymmetric reactions such as asymmetric cyclopropanation reactions, asymmetric Diels-Alder reactions, 1,3-dipolar cycloaddition reactions，asymmetric aldol addition reactions and so on in recent years.
Key words: pyridine-2,6-bis(oxazolines), chiral catalysts, asymmetric catalytical reactions, metal complexes

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[ 1 ] 张秀英(Zhang X Y) , 李书静(Li S J ) , 杨林(Yang L) . 无机化学学报(Chinese Journal of Inorganic Chemistry) , 2005 , 21 :1109 —1114
[ 2 ] 唐瑞仁(Tang R R) , 严子耳(Yan Z E) , 郭灿城(Guo C C) 等.高等学校化学学报(Chemical Journal of Chinese Universities) ,2006 , 27 : 472 —477
[ 3 ] 张生勇(Zhang S Y) , 郭建权( Guo J Q) . 不对称催化反应———原理及在有机合成中的应用( Catalytic Asymmetric Reactions : Mechanism and Application in Organic Synthesis) . 北京: 科学出版社(Beijing : Science Press) , 2002. 1 —493
[ 4 ] Desimoni G, Faita G, Quadrelli P , et al . Chem. Rev. , 2003 ,103 : 3119 —3154
[ 5 ] 靳立人(Jin L R) , 郑剑峰(Zheng J F) , 黄世俊(Huang S J )等. 厦门大学学报(Journal of Xiamen University) , 2003 , 42 :741 —745
[ 6 ] Cornejo A , Fraile J M, Garcia J I , et al . Synlett , 2005 , 2321 —2324
[ 7 ] Iwasa S , Nakamura H , Nishiyama H. Heterocycles , 2000 , 52 :939 —944
[ 8 ] Iwasa S , Tsushima S , Shimada T , et al . Tetrahedron , 2002 , 58 :227 —232
[ 9 ] Iwasa S , Tsushima S , Nishiyama H , et al . Tetrahedron :Asymmetry , 2003 , 14 : 855 —865
[10] 边庆花(Bian Q H) , 乔振(Qiao Z) , 李锋(Li F) 等. 有机化学(Chinese Journal of Organic Chemistry) , 2004 , 24 : 1542 —1552
[11] Lundgren S , Lutsenko S , Jonsson C , et al . Org. Lett . , 2003 , 5 :3663 —3665
[12] Cornejo A , Martinez-Merino V , Mayoral J A , et al . J . Org.Chem. , 2005 , 70 : 5536 —5544
[13] Weissberg A , Halak B , Portnoy M. J . Org. Chem. , 2005 , 70 :4556 —4559
[14] Nishiyama H , Soeda N , Naito T , et al . Tetrahedron : Asymmetry ,1998 , 9 : 2865 —2869
[15] Provent C , Bernardinelli G, Williams A F , et al . Eur. J . Inorg.Chem. , 2001 , 1963 —1967
[16] Girard C , Kagan H B. Angew. Chem. Int . Ed. , 1998 , 37 :2923 —2959
[17] Heard P J , Tocher D A. J . Chem. Soc. Dalton Trans. , 1998 ,2169 —2176
[18] Cuervo D , Diez J , Gamasa M P , et al . Inorg. Chem. , 2002 ,41 : 4999 —5001
[19] Chelucci G, Sanna M G, Gladiali S. Tetrahedron , 2000 , 56 :2889 —2893
[20] Cornejo A , Garcia J I , Martinez-Merino V , et al .Organometallics , 2005 , 24 : 3448 —3457
[21] Park S B , Murata K, Nishiyama H. Tetrahedron : Asymmetry ,1995 , 6 : 2487 —2494
[22] Iwasa S , Takezawa F , Tsuchiya Y, et al . Chem. Commun. ,2001 , 59 —60
[23] Marcin L R , Denhart D J , Mattson R J . Org. Lett . , 2005 , 7 :2651 —2654
[24] Taylor S , Gullick J , Mc Morn P , et al . J . Chem. Soc. Perkin Trans. 2 , 2001 : 1714 —1723
[25] Desimoni G, Faita G, Guala M, et al . Tetrahedron , 2002 , 58 :2929 —2935
[26] Fukuzawa S , Matsuzawa H , Metoki K. Synlett , 2001 , 709 —711
[27] Evans D A , Wu J . J . Am. Chem. Soc. , 2003 , 125 : 10162 —10163
[28] Usuda H , Kuramochi A , Shibasaki M, et al . Org. Lett . , 2004 ,6 : 4387 —4390
[29] Evans D A , Barnes D M, Johnson J S , et al . J . Am. Chem.Soc. , 1999 , 121 : 7582 —7594
[30] Howarth J , Gillespie K. Molecules , 2000 , 5 : 993 —997
[31] Qian C T , Wang L C. Tetrahedron Lett . , 2000 , 41 : 2203 —2206
[32] Yao S , Johannsen M, Audrain H. J . Am. Chem. Soc. , 1998 ,120 : 8599 —8605
[33] Iwasa S , Tajima K, Nishiyama H. Tetrahedron Lett . , 2001 , 42 :5897 —5899
[34] Sanchez-Blanco A I , Gothelf K V , Jorgensen K A. Tetrahedron Lett . , 1997 , 38 : 7923 —7926
[35] Iwasa S , Maeda H , Nishiyama K, et al . Tetrahedron , 2002 , 58 :8281 —8287
[36] Suga H , Inoue K, Inoue S , et al . J . Org. Chem. , 2005 , 70 :47 —56
[37] Jankowska J , Mlynarski J . J . Org. Chem. , 2006 , 71 : 1317 —1321
[38] Fu F , Teo Y C , Loh T P. Tetrahedron Lett . , 2006 , 47 : 4267 —4269
[39] Loh T P , Zhou J R. Tetrahedron Lett . , 1999 , 40 : 9115 —9118
[40] Lu J , Ji S J , Loh T P , et al . Org. Lett . , 2005 , 7 : 159 —161
[41] Bayardon J , Sinou D , Desimoni G, et al . Tetrahedron :Asymmetry , 2004 , 15 : 3195 —3200
[42] Miyabe H , Matsumura A , Takemoto Y, et al . Org. Lett . , 2004 ,6 : 4631 —4634
[43] Ginotra S K, Singh V K. Tetrahedron , 2006 , 62 : 3573 —3581
[44] Aspinall H C , Bickley J F , Greeves N , et al . Organometallics ,2005 , 24 : 3458 —3467
[45] Sammis G M, Danjo H , Jacobsen E N. J . Am. Chem. Soc. ,2004 , 126 : 9928 —9929
[46] Keith J M, Jacobsen E N. Org. Lett . , 2004 , 6 : 153 —155
[47] Nishiyama H , Kondo M, Nakamura T , et al . Organometallics ,1991 , 10 : 500 —508
[48] Cuervo D , Gamasa M P , Gimeno J , et al . Organometallics ,2005 , 24 : 2224 —2232
[49] Cuervo D , Gamasa M P , Gimeno J . J . Molec. Catal . A:Chemical , 2006 , 249 : 60 —64
[50] Tse M K, Bhor S , Klawonn M, et al . Tetrahedron Lett . , 2003 ,44 : 7479 —7483
[51] Bhor S , Tse M K, Klawonn M, et al . Adv. Synth. Catal . ,2004 , 346 : 263 —267
[52] Schaus S E , Jacobsen E N. Org. Lett . , 2000 , 2 : 1001 —1004
[53] Zhou J R , Fu G C. J . Am. Chem. Soc. , 2003 , 125 : 14726 —14727
[54] Fischer C , Fu G C. J . Am. Chem. Soc. , 2005 , 127 : 4594 —4595
[55] Andreana P R , Liu C C , Schreiber S L. Org. Lett . , 2004 , 6 :4231 —4233
[56] Wei C M, Mague J T , Li C J . Proc. Natl . Acad. Sci . USA ,2004 , 101 : 5749 —5754
[57] Shi L , Tu Y Q , Wang M, et al . Org. Lett . , 2004 , 6 : 1001 —1003
[58] Bisai A , Singh V K. Org. Lett . , 2006 , 8 : 2405 —2408
[59] Yoon T P , Macmillan D W C. J . Am. Chem. Soc. , 2001 , 123 :2911 —2912
[60] Brunner H , Kagan H B , Kreutzer G. Tetrahedron : Asymmetry ,2001 , 12 : 497 —499
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