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Progress in Chemistry 2008, Vol. 20 Issue (01): 76-86 Previous Articles   Next Articles

• Review •

Organocatalytic Asymmetric Mannich Reaction

Ma Jingjun1 Li Ning1,2 Wu Qiuhua1 Zhou Xin1 Zang Xiaohuan1 Wang Chun1**   

  1. ( 1. Hebei Key Laboratory of Bioinorganic Chemistry, College of Sciences, Agricultural University of Hebei, Baoding 071001, China; 2. College of Food Science and Technology, Agricultural University of Hebei, Baoding 071001, China )
  • Received: Revised: Online: Published:
  • Contact: Wang Chun
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Organocatalytic asymmetric reaction is an increasingly active area in organic synthesis. Asymmetric Mannich reaction is a powerful tool for the synthesis of β-amino-carbonyl compounds. The reported organocatalyst for asymmetric Mannich reaction include proline derivatives, chiral phosphoric acids, chiral (thio)urea derivatives, cinchona alkaloids and so on, which can catalyze the asymmetric Mannich reaction with high catalytic activity and excellent enantiselectivity. The applications of various organocatalysts in asymmetric Mannich reaction are reviewed in this paper. The reaction mechanism, catalytic activity and the asymmetric induction influenced by the structure of organocatalysts and the reaction condition also discussed.

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[ 1 ] List B , Lerner R A , Barbas C F III. J . Am. Chem. Soc. , 2000 ,122 (10) : 2395 —2396
[ 2 ] Ahrendt K A , Borths C J , MacMillan D W C. J . Am. Chem.Soc. , 2000 , 122 (17) : 4243 —4244
[ 3 ] Yang D. Acc. Chem. Res. , 2004 , 37(8) : 497 —505
[ 4 ] Shi Y. Acc. Chem. Res. , 2004 , 37(8) : 488 —496
[ 5 ] Sigman M S , Jacobsen E N. J . Am. Chem. Soc. , 1998 , 120(19) : 4901 —4902
[ 6 ] 王春(Wang C) , 高勇军( Gao Y J ) , 张英群(Zhang Y Q) 等.化学进展(Progress in Chemistry) , 2006 , 18(6) : 761 —767
[ 7 ] Berkesssel A , Grêger H. Asymmetric Organocatalysis , from Biomimetic Concept to Application in Asymmetric Synthesis.Weinheim: Wiley-VCH , 2005
[ 8 ] Special Issue : Asymmetric Organocatalysis , Acc. Chem. Res. ,2004 , 37(8) : 487 —631
[ 9 ] List B. J . Am. Chem. Soc. , 2000 , 122 (38) : 9336 —9337.
[10] List B , Pojarliev P , Biller W T , et al . J . Am. Chem. Soc. ,2002 , 124 (5) : 827 —833
[11] Wang K C. Chin. Pharm. J . , 2003 , 55(2) : 87 —99
[12] Ibrahem I , Zou W B , Casas J , et al . Tetrahedron , 2006 , 62(2/3) : 357 —364
[13] Notz W, Tanaka F , Watanabe S , et al . J . Org. Chem. , 2003 ,68(25) : 9624 —9634
[14] Córdova A , Watanabe S , Tanaka F , et al . J . Am. Chem. Soc. ,2002 , 124 (9) : 1866 —1867
[15] Hayashi Y, Tsuboi W, Ashimine I , et al . Angew. Chem. Int .Ed. , 2003 , 42(31) : 3677 —3680
[16] Hayashi Y, Tsuboi W, Ashimine I , et al . Angew. Chem. , 2003 ,115(31) : 3805 —3808
[17] Córdova A. Synlett , 2003 , 11 : 1651 —1654
[18] Chowdari N S , Suri J T , Barbas C F Ⅲ. Org. Lett . , 2004 , 6(15) : 2507 —2510
[19] Ma J J , Zhou X, Zang X H , et al . Aus. J . Chem. , 2007 , 60 :146 —148
[20] Sheldon R A. Chem. Commun. , 2001 , 2399 —2407
[21] Chowdari N S , Ramachary D B , Barbas C F Ⅲ. Synlett , 2003 ,12 : 1906 —1909
[22] Córdova A , Barbas C F Ⅲ. Tetrahedron Lett . , 2003 , 44 (9) :1923 —1926
[23] Hayashi Y, Tsuboi W, Shoji M, et al . J . Am. Chem. Soc. ,2003 , 125 (37) : 11208 —11209
[24] Rodriguez B , Bolm C. J . Org. Chem. , 2006 , 71 (7) : 2888 —2891
[25] Cobb A J A , Shaw D M, Longbottom D A , et al . Org. Biomol .Chem. , 2005 , 3(1) : 84 —96
[26] Cobb A J A , Shaw D M, Ley S V. Synlett , 2004 , 3 : 558 —560
[27] Córdova A , Barbas C F Ⅲ. Tetrahedron Lett . , 2002 , 43 (43) :7749 —7752
[28] Mitsumori S , Zhang H , Cheong P H Y, et al . J . Am. Chem.Soc. , 2006 , 128 (4) : 1040 —1041
[29] Zhang H , Mifsud M, Tanaka F , et al . J . Am. Chem. Soc. ,2006 , 128 (30) : 9630 —9631
[30] Cheong P H Y, Zhang H , Thayumanavan R , et al . Org. Lett . ,2006 , 8(5) : 811 —814
[31] Akiyama T , Itoh J , Fuchibe K. Adv. Synth. Catal . , 2006 , 348(9) : 999 —1010
[32] Taylor M S , Jacobsen E N. Angew. Chem. Int . Ed. , 2006 , 45(10) : 1520 —1543
[33] Connon S J . Chem. Eur. J . , 2006 , 12(21) : 5418 —5427
[34] Bolm C , Rantanen T , Schiffers I , et al . Angew. Chem. Int .Ed. , 2005 , 44(12) : 1758 —1763
[35] Akiyama T , Itoh J , Yokata K, et al . Angew. Chem. Int . Ed. ,2004 , 43(12) : 1566 —1568
[36] Uraguchi D , Terada M. J . Am. Chem. Soc. , 2004 , 126 (17) :5356 —5357
[37] Akiyama T , Saitoh Y, Morita H , et al . Adv. Synth. Catal . ,2005 , 347 (11/13) : 1523 —1526
[38] Hoashi Y, Yabuta T , Takemoto Y. Tetrahedron Lett . , 2004 , 45(50) : 9185 —9188
[39] Wenzel A G, Lalonde M P , Jacobsen E N. Synlett , 2003 , 12 :1919 —1922
[40] Lou S , Taoka B M, Ting A , et al . J . Am. Chem. Soc. , 2005 ,127(32) : 11256 —11257
[41] Ting A , Lou S , Schaus S E. Org. Lett . , 2006 , 8(10) : 2003 —2006
[42] Tillman A L , Ye J X, Dixon D J . Chem. Commun. , 2006 ,1191 —1193
[43] Song J , Wang Y, Deng L. J . Am. Chem. Soc. , 2006 , 128(18) : 6048 —6049
[44] Song J , Shih H W, Deng L. Org. Lett . , 2007 , 9(4) : 603 —606

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