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Progress in Chemistry 2008, Vol. 20 Issue (10): 1534-1543 Previous Articles   Next Articles

• Review •

Application of Chiral Phosphoric Acid in Asymmetric Synthesis

Chen Xiaofen; Liu Zenglu; Mao Zhenmin*   

  1. (School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, China)
  • Received: Revised: Online: Published:
  • Contact: Mao Zhenmin
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The chiral phosphoric acid is a fairly strong Bronsted acid with novel structure which was first reported in 2004. It has been developed rapidly in recent years and become a very important branch of organocatalysis. Excellent enantioselectivities and good yields can be obtained in a series of asymmetric addition and reduction reactions of imines when catalyzed by chiral phosphoric acid catalysts, such as Mannich reaction, asymmetric transfer hydrogenation reaction, hydrophosphonylation reaction, Pictet-Spengler reaction, Strecker reaction, aza-Diels-Alder reaction, Friedel-Craft reaction, alkylation of diazoester reaction and so on. In this paper, the latest progress in the research of chiral phosphoric acid catalysts for relevant asymmetric reactions is reviewed.

Key words: chiral phosphoric acid, imines, asymmetric catalysis

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[ 1 ] 傅滨(Fu B) , 肖玉梅(Xiao Y M) , 李楠(Li N) 等. 有机化学(Organic Chemistry) , 2006 , 26 : 899 —905
[ 2 ] Connon S J . Angew. Chem. Int . Ed. , 2006 , 45 : 3909 —3912
[ 3 ] Akiyama T , Itoh J , Yokota K, Fuchibe K. Angew. Chem. Int .Ed. , 2004 , 43 : 1566 —1568
[ 4 ] Yamanaka M, Itoh J , Akiyama T , et al . J . Am. Chem. Soc. ,2007 , 129 : 6756 —6764
[ 5 ] Akiyama T , Saitoh Y, Fuchibe K, et al . Adv. Synth. Catal . ,2005 , 347 : 1523 —1526
[ 6 ] Uraguchi D , Terada M. J . Am. Chem. Soc. , 2004 , 126 :5356 —5375
[ 7 ] Guo Q X, Liu H , Gong L Z , et al . J . Am. Chem. Soc. , 2007 ,129 : 3790 —3791
[ 8 ] Storer R I , Carrera D E , MacMillan D W C , et al . J . Am.Chem. Soc. , 2006 , 128 : 84 —86
[ 9 ] Hoffmann S , Nicoletti M, List B. J . Am. Chem. Soc. , 2006 ,128 : 13074 —13075
[10] Rueping M, Sugiono E , Bolte M. Org. Lett . , 2005 , 7 :3781 —3783
[11] Hoffmann S , Swayad A M, List B. Angew. Chem. Int . Ed. ,2005 , 44 : 7424 —7427
[12] Rueping M, Antonchick A P , Theissmann T. Angew. Chem. Int .Ed. , 2006 , 45 : 3683 —3686
[13] Rueping M, Antonchick A P , Theissmann T. Angew. Chem. Int .Ed. , 2006 , 45 : 6751 —6755
[14] RuepingM, Antonchick A P. Angew. Chem. Int . Ed. , 2007 ,46 : 4562 —4565
[15] Li G L , Liang Y X, Antilla J C. J . Am. Chem. Soc. , 2007 ,129 : 5830 —5831
[16] Akiyama T , Morita H , Fuchibe K, et al . Org. Lett . , 2005 , 7 :2583 —2585
[17] Seayad J , Seayad A M, List B. J . Am. Chem. Soc. , 2006 ,128 :1086 —1087
[18] Rueping M, Sugiono E , Azap C. Angew. Chem. Int . Ed. ,2006 , 45 : 2617 —2619
[19] Rowland G B , Zhang H , Antilla J C , et al . J . Am. Chem.Soc. , 2005 , 127 : 15696 —15697
[20] Chen X H , Xu X Y, Gong L Z , et al . J . Am. Chem. Soc. ,2006 , 128 : 14802 —14803
[21] Terada M, Sorimachi K. J . Am. Chem. Soc. , 2007 , 129 :292 —293
[22] Kang Q , Zhao Z A , You SL. J . Am. Chem. Soc. , 2007 , 129 :1484 —1485
[23] Wang Y Q , Song J , Deng L , et al . J . Am. Chem. Soc. , 2006 ,128 : 8156 —8157
[24] Rowland G B , Rowland E B , Antilla J C , et al . Org. Lett . ,2007 , 9 : 2609 —2611
[25] Jia Y X, Zhong J , Zhou Q L , et al . Angew. Chem. Int . Ed. ,2007 , 46 : 5565 —5567
[26] Uraguchi D , Sorimachi K, Terada M. J . Am. Chem. Soc. ,2004 , 126 : 11804 —11805
[27] Akiyama T , Tamura Y, Itoh J , et al . Synlett , 2006 , ( 1) :141 —143
[28] Akiyama T , Itoh J , Fuchibe K. Angew. Chem. Int . Ed. , 2006 ,45 : 4796 —4798
[29] Josephsohn N S , Snapper M L , Hoveyda A H. J . Am. Chem.Soc. , 2003 , 125 : 4018 —4019
[30] Ishitani H , Kobayashi S. Tetrahedron Lett . , 1996 , 37 :7357 —7360
[31] Sundararajan G, Prabagaran N , Varghese B. Org. Lett . , 2001 ,3 : 1973 —1976
[32] Akiyama T , Morita H , Fuchibe K. J . Am. Chem. Soc. , 2006 ,128 : 13070 —13071
[33] Rueping M, Azap C. Angew. Chem. Int . Ed. , 2006 , 45 :7832 —7835
[34] Liu H , Cun L F , Gong L Z , et al . Org. Lett . , 2006 , 8 :6023 —6026
[35] Matsubara R , Vital P , Kobayashi S , et al . Tetrahedron , 2004 ,60 : 9769 —9784
[36] Teradan M, Machioka K, Sorimachi K. Angew. Chem. Int .Ed. , 2006 , 45 : 2254 —2257
[37] Uraguchi D , Sorimachi K, Terada M. J . Am. Chem. Soc. ,2005 , 127 : 9360 —9361
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