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Progress in Chemistry 2010, Vol. 22 Issue (07): 1353-1361 Previous Articles   Next Articles

• Invited Article •

Asymmetric Reactions Catalyzed by Chiral Tridentate Schiff Base-Metal Complexes

Lin Lili    Liu Xiaohua    Feng XIiaoming**   

  1. (College of Chemistry, Sichuan University, Chengdu 610064, China)
  • Received: Online: Published:
  • Contact: Feng XIiaoming E-mail:xmfeng@scu.edu.cn
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The chiral tridentate Schiff bases, which derived from various chiral amino alcohols and salicylaldehyde derivatives, complexed with metals, such as Ti, Cr, V, Cu, Fe and Al, have shown catalytic ability in many asymmetric reactions. Especially in asymmetric trimethylsilylcyanation of aldehydes, Diels-Alder reaction, aldol reaction, hetro-ene reaction and sulfide oxidation reaction, systematic work has been reported. The development of the work was described in this review, meanwhile, the catalytic activity and enantioselectivity infuenced by the structure of catalyst and reaction condition were also discussed.

Contents 
1 Introduction 
2 Asymmetric reactions catalyzed by Schiff base titanium complexes 
3 Asymmetric reactions catalyzed by Schiff base chromium complexes
4 Asymmetric reactions catalyzed by Schiff base vanadium and iron complexes 
5 Asymmetric reactions catalyzed by Schiff base copper and aluminum complexes 
6 Conclusions and outlook

CLC Number: 

[1 ] 林国强( Lin G Q) ,陈耀全( Chen Y Q) ,李月明( Li Y M) ,
陈新滋( Chen X Z) . 手性合成( Chiral Synthesis) . 北京: 科学
出版社( Beijing:Science Press) ,2007
[2 ] Hayashi M,Miyamoto Y,Inoue T,Oguni N. J. Chem. Soc.
Chem. Commun. ,1991,1752—1753
[3 ] Hayashi M,Miyamoto Y,Inoue T,Oguni N. J. Org. Chem. ,
1993,58: 1515—1522
[4 ] Flores-Lopéz L Z,Parra-Hake M,Somanathan R,Walsh P J.
Organometallics,2000,19: 2153—2160
[5 ] Gama A, Flores-Lopéz L Z, Aguirre G, Parra-Hake M,
Somanathan R,Walsh P J. Tetrahedron: Asymmetry,2002,13:
149—154
[6 ] Jiang Y, Zhou X, Hu W, Wu L, Mi A. Tetrahedron:
Asymmetry,1995,6: 405—408
[7 ] 蒋耀忠( Jiang Y Z) ,宓爱巧(Mi A Q) ,胡文浩( Hu W H) ,
陈代谟( Chen D M) ,王朝阳(Wang Z Y) ,邓金根( Deng J
G) ,楼荣良( Lou R L) ,张晓梅( Zhang X M) . 分子催化
( Journal of Molecular Catalysis) ,1997,11: 401—407
[8 ] Hayashi M, Inoue T, Oguni N. J. Chem. Soc. Chem.
Commun. ,1994,341—342
[9 ] Hayashi M, Inoue T,Miyamoto Y, Oguni N. Tetrahedron,
1994,50: 4385—4398
[10] Hayashi M,Kaneda H,Oguni N. Tetrahedron: Asymmetry,
1995,6: 2511—2516
[11] Carreira E M,Lee W,Singer R A. J. Am. Chem. Soc. ,1994,
116: 8837—8838
[12] Carreira E M,Lee W,Singer R A. J. Am. Chem. Soc. ,1995,
117: 3649—3650
[13] Singer R A,Carreira E M. J. Am. Chem. Soc. ,1995,117:
12360—12361
[14] Yuan Y,Li X,Sun J,Ding K. J. Am. Chem. Soc. ,2002,
124: 14866—14867
[15] Yuan Y,Long J,Sun J,Ding K. Chem. Eur. J. ,2002,8:
5033—5042
[16] Ji B,Yuan Y,Ding K,Meng J. Chem. Eur. J. ,2003,9:
5989—5996
[17] Fan Q,Lin L L,Liu J,Huang Y Z,Feng X M,Zhang G L.
Org. Lett. ,2004,6: 2185—2188
[18] Fan Q,Lin L L,Liu J,Huang Y Z,Feng X M. Eur. J. Org.
Chem. ,2005,3542—3552
[19] Bensari A,Renaud J L,Riant O. Org. Lett. ,2001,3: 3863—
3865
[20] Li Z, Fernández M, Jacobsen E N. Org. Lett. ,1999,1:
1611—1613
[21] Dossetter A G,Jamison T F,Jacobsen E N. Angew. Chem. Int.
Ed. ,1999,38: 2398—2400
[22] Gademann K,Chavez D E,Jacobsen E N. Angew. Chem. Int.
Ed. ,2002,41: 3059—3061
[23] Jarvo E R,Lawrence B M,Jacobsen E N. Angew. Chem. Int.
Ed. ,2005,44: 6043—6046
[24] Boezio A A,Jarvo E R,Lawrence B M,Jacobsen E N. Angew.
Chem. Int. Ed. ,2005,44: 6046—6050
[25] Ruck R T,Jacobsen E N. J. Am. Chem. Soc. ,2002,124:
2882—2883
[26] Ruck R T,Jacobsen E N. Angew. Chem. Int. Ed. ,2003,42:
4771—4774
[27] Grachan M L,Tudge M T,Jacobsen E N. Angew. Chem. Int.
Ed. ,2008,47: 1469—1472
[28] Bolm C,Bienewald F. Angew. Chem. Int. Ed. ,1995,34:
2640—2642
[29] Liu G,Cogan D A,Ellman J A. J. Am. Chem. Soc. ,1997,
119: 9913—9914
[30] Cogan D A,Liu G,Kim K,Backes B J,Ellman J A. J. Am.
Chem. Soc. ,1998,120: 8011—8019
[31] Legros J,Bolm C. Angew. Chem. Int. Ed. ,2003,42: 5487—
5489
[32] Blanc A,Toste F D. Angew. Chem. Int. Ed. ,2006,45:
2096—2099
[33] Aratani T,Yoneyoshi Y,Nagase T. Tetrahedron Letters,1975,
16:1707—1710
[34] Lin L L,Fan Q,Qin B,Feng X M. J. Org. Chem. ,2006,71:
4141—4146
[35] Zhou X,Liu X,Yang X,Shang D,Xin J,Feng X. Angew.
Chem. Int. Ed. ,2008,47: 392—394

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