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Progress in Chemistry 2011, Vol. 23 Issue (5): 903-913 Previous Articles   Next Articles

• Review •

Asymmetric Synthesis of Chiral Aryl Vicinal Diols

Liu Xiang1, Pan Zhengguang1, Xu Jianhe2   

  1. 1. School of Chemical and Material Engineering, Jiangnan University, Wuxi 21412;
    2. State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
  • Received: Revised: Online: Published:
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Chiral aryl vicinal diols with special functional group are potentially valuable synthetic intermediates for the preparation of pharmaceuticals, agrochemicals and pheromones. In recent years, the synthesis and application of chiral aryl vicinal diols have attracted intensive attention of chemists. Recent progress in asymmetric synthesis of chiral aryl vicinal diols is reviewed in both biocatalytic and chemocatalytic perspectives. The effects of some factors, including the electronic effects and steric factors of substituted groups, the species of chiral catalysts and the different reaction media, on the yields and optical activity of chiral aryl vicinal diols are summarized. The trends in the asymmetric synthesis of chiral aryl vicinal diols are prospected.

Key words: chiral aryl vicinal diols, asymmetric synthesis, biocatalysis, chemocatalysis

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[1] Schoemaker H E, Mink D, Wubbolts M G. Science, 2003, 299: 1694-1697
[2] Pye P J, Rossen K, Weissman S A, Maliakal A, Reamer R A, Ball R, Tsou N N, Volante R P, Reider P J. Chem. Eur. J., 2002, 8(6): 1372-1376
[3] Haukaas M H, O'Doherty G A. Org. Lett., 2002, 4(10): 1771- 1774
[4] 林国强(Lin G Q), 王梅祥(Wang M X), 杜灿屏(Du C P), 吴镭(Wu L). 手性合成与手性药物(Chiral Synthesis and Chiral Drug). 北京: 化学工业出版社(Chemical Industry Press), 2008. 24-24
[5] Jur ek O, Wimmerová, M, Wimmer Z. Coordin. Chem. Rev., 2008, 252: 767-781
[6] 刘湘(Liu X), 张宝立(Zhang B L), 夏永梅(Xia Y M), 许建和(Xu J H). 化学进展(Progress in Chemistry), 2008, 20: 1108-1114
[7] Kroutil W, Mang H, Edegger K, Faber K. Curr. Opin. Chem. Biol., 2004, 8: 120-126
[8] 刘湘(Liu X), 张宝立(Zhang B L), 夏永梅(Xia Y M), 许建和(Xu J H). 化学学报(Acta Chimica Sinica), 2009, 67(13): 1492-1496
[9] Zhang R Z, Xu Y, Geng Y W, Wang S S, Sun Y, Xiao R. Appl. Biochem. Biotechnol., 2010, 160: 868-878
[10] Nie Y, Xu Y, Lv T F, Xiao R. J. Chem. Technol. Biotechnol., 2009, 84: 468-472
[11] Hu Q S, Xu Y, Nie Y. J. Chem. Technol. Biotechnol., 2010, 85: 252-257
[12] Hu Q S, Xu Y, Nie Y. Bioresour. Technol., 2010, 101: 8461-8463
[13] Zhang R Z, Xu Y, Sun Y, Zhang W C, Xiao R. Appl. Environ. Microbiol., 2009, 75(7): 2176-2183
[14] Andrade L H, Polak R, Porto A L M, Schoenlein-Crusius I H, Comasseto J V. Lett. Org. Chem., 2006, 3(8): 613-618
[15] Liu X, Pan Z G, Xu J H, Li H X. Chin. Chem. Lett., 2010, 21: 305-308
[16] Boyd D R, Sharma N D, Bowers N I, Brannigan I N, Groocock M R, Malone J F, McConville G, Allen C C R. Adv. Synth. Catal., 2005, 347: 1081-1089
[17] Steinreiber A, Faber K. Curr. Opin. Biotechnol., 2001, 12: 552-558
[18] 贾会坤(Jia H K), 张奕南(Zhang Y N), 冯进辉(Feng J H), 许平(Xu P). 化学进展(Progress in Chemistry), 2007, 19: 1223-1228
[19] Xu W, Xu J H, Pan J, Gu Q, Wu X Y. Org. Lett., 2006, 8(8): 1737-1740
[20] Cao L, Lee J, Chen W, Wood T K. Biotechnol. Bioeng., 2006, 94(3): 522-529
[21] Kim H S, Lee O K, Hwang S, Kim B J, Lee E Y. Biotechnol. Lett., 2008, 30: 127-133
[22] Hwang S, Choi C Y, Lee E Y. Biotechnol. Bioprocess Eng., 2008, 13: 453-457
[23] Yeates C A, Smit M S, Botes A L, Breytenbach J C, Krieg H M. Enzyme Microb. Technol., 2007, 40: 221-227
[24] Liu Z Y, Michel J, Wang Z S, Witholt B, Li Z. Tetrahedron: Asymmetry, 2006, 17: 47-52
[25] Deregnaucourt J, Archelas A, Barbirato F, Paris J M, Furstoss R. Adv. Synth. Catal., 2007, 349: 1405-1417
[26] Karboune S, Archelas A, Baratti J C. Process Biochem., 2010, 45: 210-216
[27] Hasnaoui G, Spelberg J H L, Vries E, Tang T X, Hauer B, Janssen B D. Tetrahedron: Asymmetry, 2005, 16: 1685-1692
[28] Xu Y, Jia X, Panke S, Li Z. Chem. Commun., 2009, 1481-1483
[29] 李明月(Li M Y), 范青华(Fan Q H), 陈新滋(Chen X Z). 不对称有机反应(Asymmetric Organic Reaction). 北京: 化学工业出版社(Chemical Industry Press), 2005. 11-29
[30] Wai J S M, Marko I, Svendsen J S, Finn M G, Jacobsen E N, Sharpless K B. J. Am. Chem. Soc., 1989, 111: 1123-1125
[31] Jacobsen E N, Marko I, France M B, Svendsen J S, Sharpless K B. J. Am. Chem. Soc., 1989, 111: 737-739
[32] Jiang R, Kuang Y Q, Sun X L, Zhang S Y. Acta Chim. Slov., 2005, 52: 467-470
[33] 程司堃(Chen S K), 张生勇(Zhang S Y), 王平安(Wang P A), 孙晓莉(Sun X L), 赵燕(Zhao Y). 高等学校化学学报(Chemical Journal of Chinese Universities), 2006, 27(2): 250-253
[34] Choi D S, Han S S, Kwueon E K, Choi H Y, Hwang S H, Park Y S, Song C E. Adv. Synth. Catal., 2006, 348: 2560-2564
[35] 金瑛(Jin Y), 姚志军(Yao Z J), 张生勇(Zhang S Y), 姜茹(Jiang R), 孙晓莉(Sun X L). 有机化学(Chinese Journal of Organic Chemistry), 2007, 27(5): 602-606
[36] Dehury S D, Hariharakrishnan V S. Tetrahedron Lett., 2007, 48: 2493-2496
[37] Junttila M H, Hormi O O E. J. Org. Chem., 2009, 74(8): 3038-3047
[38] Chen H, Wang Q F, Sun X L, Luo J, Jiang R. Mendeleev Commun., 2010, 20: 104-105
[39] Tang W, Zhang X. Chem. Rev., 2003, 103: 3029-3070
[40] Blaser H U, Schmidt E. Asymmetric Catalysis on Industrial Scale. Weiheim: Wiley-VCH, 2004
[41] 张文虎(Zhang W H), 蔡燕(Cai Y), 刘湘(Liu X), 方云(Fang Y), 许建和(Xu J H). 化学进展(Progress in Chemistry), 2007, 19(10): 1537-1552
[42] Sonderegger O J, Ho G M W, Bürgi T, Baiker A. J. Catal., 2005, 230: 499-506
[43] Matharu D S, Morris D J, Clarkson G J, Wills M. Chem. Commun., 2006, 3232-3234
[44] Boaz N W, Ponasik J A, Large S E. Tetrahedron Lett., 2006, 47: 4033-4035
[45] Ohkuma T, Utsumi N, Watanabe M, Tsutsumi K, Arai N, Murata K. Org. Lett., 2007, 9(13): 2565-2567
[46] Kadyrov R, Koenigs R M, Brinkmann C, Voigtlaender D, Rueping M. Angew. Chem. Int. Ed., 2009, 48: 7556-7559
[47] 蒋成君(Jiang C J), 陈志荣(Chen Z R). 化学进展(Progress in Chemistry), 2008, 20(9): 1294-1305
[48] 王磊(Wang L), 李叶芝(Li Y Z), 黄化民(Huang H M), 方唯硕(Fang W S). 有机化学(Chinese Journal of Organic Chemistry), 2006, 26(9): 1208-1216
[49] Breinbauer R, Jacobsen E N. Angew. Chem. Int. Ed., 2000, 39: 3604-3607
[50] Rossbach B M, Leopold K, Weberskirch R. Angew. Chem. Int. Ed., 2006, 45: 1309-1312
[51] Zheng X L, Jones C W, Weck M. Adv. Synth. Catal., 2008, 350: 255-261
[52] Andrews P C, Fraser B H, Gee W J, Giera D, Junk P C, Massi M, Tuck K L. Polyhedron., 2010, 29: 1764-1770
[53] Singh S, Duffy C D, Shah S T A, Guiry P J. J. Org. Chem., 2008, 73: 6429-6432
[54] Alberti M N, Vassilikogiannakis G, Orfanopoulos M. Org. Lett., 2008, 10(18): 3997-4000
[55] Ishihara K, Kosugi Y, Sakakura A. Org. Lett., 2008, 10(15): 3191-3194
[56] Zhang P W, Terefenko E A, Bray J, Deecher D, Fensome A, Harrison J, Kim C. J. Med. Chem., 2009, 52: 5703-5711
[57] Grǒger H, Chamouleau F, Orologas N, Rollmann C, Drauz K, Hummel W, Weckbecker A, May O. Angew. Chem. Int. Ed., 2006, 45: 5677-5681
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