English
新闻公告
More
化学进展 2007, Vol. 19 Issue (05): 745-750 前一篇   后一篇

• 综述与评论 •

手性亚砜合成*

曾庆乐**   

  1. 成都理工大学材料与化学化工学院化工与制药系 成都 610059
  • 收稿日期:2006-07-19 修回日期:2006-08-22 出版日期:2007-05-24 发布日期:2007-05-24
  • 通讯作者: 曾庆乐

Synthesis of Chiral Sulfoxides

Zeng Qingle**   

  1. Department of Chemical Engineering and Pharmaceutics, College of Material and Chemistry & Chemical Engineering , Chengdu University of Technology, Chengdu 610059, China
  • Received:2006-07-19 Revised:2006-08-22 Online:2007-05-24 Published:2007-05-24
手性亚砜及其衍生物广泛作为重要手性中间体和辅剂、手性配体和催化剂、手性药物。手性亚砜可以采用生物方法和化学方法来合成,化学方法包括手性辅剂诱导、手性氧化剂氧化、手性拆分和不对称催化等。本文简要综述了手性亚砜的各种用途和各种合成方法的研究进展,主要介绍了钛和钒催化的不对称硫醚氧化反应,也介绍了作者最近在钒催化的不对称硫醚氧化反应方面所做的研究工作。
Chiral sulfoxides and their derivatives are extensively used as important chiral intermediates and auxiliaries, chiral ligands and catalysts, and chiral drugs. Chiral sulfoxides may be obtained by biological and chemical methods. The chemical methods include chiral auxiliary's induction, chiral oxidant's oxidation, chiral resolution, and enantioselective catalysisi. The applications and research advance of various synthetic methods of chiral sulfoxides, introduction of titanium-, vanadium-catalyzed enantioselective sulfoxidation, as well as author's recent research work about vanadium-catalyzed sulfoxidation are reviewed in this paper.

中图分类号: 

()

[ 1 ] Fernandez I , Khiar N. Chem. Rev. , 2003 , 103 : 3651 —3705
[ 2 ] Legros J , Dehli J R , Bolm C. Adv. Synth. Catal . , 2005 , 347 :19 —31
[ 3 ] Jacobsen E N , Pfaltz A , Yamamoto H. Comprehensive Asymmetric Catalysis. Berlin : Springer , 1999. 697
[ 4 ] 李树坤(Li S K) , 白东鲁(Bai D L) . 化学进展( Progress in Chemistry) , 2001 , 13(5) : 351 —359
[ 5 ] 黄秋亚(Huang Q Y) , 朱槿(Zhu J) , 邓金根(Deng J G) . 有机化学(Chin. J . Org. Chem. ) , 2005 , 25 : 496 —506
[ 6 ] Kobayashi S , Ogawa C , Konishi H , Sugiura M. J . Am. Chem.Soc. , 2003 , 125 : 6610 —6611
[ 7 ] Bolm C , Simic O. J . Am. Chem. Soc. , 2001 , 123 : 3830 —3831
[ 8 ] Cho G Y, Bolm C. Org. Lett . , 2005 , 7 : 4983 —4985
[ 9 ] Rouhi A M. Chem. Eng. News , 2003 , 81 : 56 —61
[10] Andersen K K, Gaffield W L , Papanikolau N E , Foley J W,Perkins R I. J . Am. Chem. Soc. , 1964 , 86 : 5637 —5646
[11] Lu B Z , Jin F Q , Zhang Y D , Wu X H , Wald S A , Senanayake C H. Organ. Lett . , 2005 , 7 : 1465 —1684
[12] Qin Y, Wang C H , Huang Z Y, Xiao X, Jiang Y Z. J . Org.Chem. , 2005 , 69 : 8533 —8536
[13] Lattanzi A , Iannece P , Scettri A. Tetrahedron : Asymm. , 2004 ,15 : 413 —418
[14] Toda F , Tanaka K, Nagamatsu S. Tetrahedron Lett . , 1984 , 25 :4929 —4932
[15] Zhu J , Qin Y, He Z , Fu F M, Zhou Z Y, Deng J G, Jiang Y Z ,Chau T Y. Tetrahedron : Asymm. , 1997 , 8 : 2505 —2508
[16] Deng J G, Chi Y X, Fu F M, Cui X, Yu KB , Zhu J , Jiang Y Z. Tetrahedron : Asymm. , 2000 , 11 : 1729 —1732
[17] Liao J , Sun X X, Cui X, Yu K B , Zhu J , Deng J G. Chem.Eur. J . , 2003 , 9 : 2611 —2615
[18] Scarso A , Strukul G. Adv. Synth. Catal . , 2005 , 347 : 1227 —1234
[19] Pitchen P , Deshmukh M N , Dunach E , Kagan H B. J . Am.Chem. Soc. , 1984 , 106 : 8188 —8193
[20] Brunel J M, Kagan H B. Synlett , 1996 , 404 —406
[21] Komatsu N , Hashizume M, Sugita T , Uemura S. J . Org.Chem. , 1993 , 58 : 7624 —7626
[22] Jia X, Li X, Xu L , Li Y, Shi Q , Au-Yeung T T L , Yip C W,Yao X, Chan A S C. Adv. Synth. Catal . , 2004 , 346 : 723 —726
[23] 彭云贵(Peng Y G) , 冯小明(Feng X M) , 崔欣(Cui X) , 蒋耀忠(Jiang Y Z) . 高等学校化学学报(Chem. J . Chin. Univ. ) ,2001 , 22 : 1326 —1331
[24] 彭云贵(Peng Y G) , 冯小明(Feng X M) , 崔欣(Cui X) , 蒋耀忠(Jiang Y Z) . 有机化学(Chin. J . Org. Chem. ) , 2004 , 24 :558 —562
[25] Bonchio M, Licini G, Modena G, Moro S , Bortolini O , Traldi P ,Nugent WA. Chem. Commun. , 1997 , 869 —870
[26] Saito B , Katsuki T. Tetrahedron Lett . , 2001 , 42 : 3873 —3876
[27] Nakajima K, Kojima M, Toriumi K, Saito K, Fujita J . Bull .Chem. Soc. Jpn. , 1989 , 62 : 760 —767
[28] Bolm C , Bienewald F. Angew. Chem. Int . Ed. Engl . , 1996 ,34 : 2640 —2642
[29] Vetter A H , Berkessel A. Tetrahedron Lett . , 1998 , 39 : 1741 —1744
[30] Ohta C , Shimizu H , Kondo A , Katsuki T. Synlett , 2002 , 161 —163
[31] Jeong Y C , Choi S , Hwang Y D , Ahn K H. Tetrahedron Lett . ,2004 , 45 : 9249 —9252
[32] Jeong Y C , Huang Y D , Choi S , Ahn K H. Tetrahedron :Asymm. , 2005 , 16 : 3497 —3501
[33] Pelotier B , Anson M S , Campbel I B , Macdonald S J F , Priem G, Jackson R F W. Synlett , 2002 , 1055 —1060
[34] Cucciolito M E , Del Litto R , Roviello G, Ruffo F. J . Mol .Catal . A: Chem. , 2005 , 236 : 176 —181
[35] Zeng Q L , Mi A Q , Jiang Y Z , et al . Tetrahedron : Asymm. ,2002 , 13(2) : 115 —117
[36] Zeng Q L , Mi A Q , Jiang Y Z , et al . Tetrahedron , 2002 , 58 :8799 —8803
[37] Weng W, Wang Q H , Yao B X, Zeng Q L. J . Chromatogr. , A ,2004 , 1042 : 81 —87
[38] 曾庆乐(Zeng Q L) , 宓爱巧(Mi A Q) , 蒋耀忠(Jiang Y Z) .化学进展(Progress in Chemistry) , 2004 , 16 : 603 —612
[39] 曾庆乐(Zeng Q L) , 崔欣(Cui X) , 韩颖(Han Y) , 蒋耀忠(Jiang Y Z) . 合成化学(Chin. J . Synth. Chem. ) , 2002 , 10 :95 —97
[40] Zeng Q L , Wang H Q , Wang T J , Cai YM, Weng W, Zhao Y F. Adv. Synth. Catal . , 2005 , 347 (15) : 1933 —1936
[41] Zeng Q L , Chen W Z , Zhao Y F. Int . J . Mass Spectrom. , 2007 ,262 : 161 —167
[42] Drago C , Caggiano L , Jackson R F W. Angew. Chem. Int . Ed. ,2005 , 44 : 7221 —7223
[43] Balcells D , Maseras F , Ujaque G. J . Am. Chem. Soc. , 2005 ,127 : 3624 —3634
[44] Zeng Q L , Wang H Q , Weng W, Lin W S , Gao Y X, Huang X T , Zhao Y F. New J . Chem. , 2005 , 29(9) : 1125 —1127
[45] Nakajima K, Kojima M, Fujita J . Chem. Lett . , 1986 , 1483 —1486
[46] Sun J T , Zhu C J , Dai Z Y, Yang M H , Pan Y, Hu H W. J .Org. Chem. , 2004 , 69 : 8500 —8503
[47] Palucki M, Hanson P , Jacobsen E N. Tetrahedron Lett . , 1992 ,33 : 7111 —7114
[48] Noda K, Hosoya N , Irie R , Yamashita Y, Katsuki T.Tetrahedron , 1994 , 50 : 9609 —9618
[49] Kokubo C , Katsuki T. Tetrahedron , 1996 , 52 : 13895 —13900
[50] Noda K, Hosoya N , Yanai K, Irie R , Katsuki T. Tetrahedron Lett . , 1994 , 35 : 1887 —1890
[51] Mekmouche Y, Hummel H , Ho R Y N , et al . Chem. Eur. J . ,2002 , 8 : 1196 —1204
[52] Legros J , Bolm C. Angew. Chem. Int . Ed. , 2004 , 43 : 4225 —4228
[53] Thakur V V , Sudalai A. Tetrahedron : Asymm. , 2003 , 14 :407 —410

[1] 高珊 曾庆乐 唐红艳 刘洋 董俊宇 张斌彬. 钛催化不对称硫醚氧化合成手性药物*[J]. 化学进展, 2010, 22(09): 1760-1766.
[2] 李树坤,白东鲁. 手性亚砜在不对称合成中的应用[J]. 化学进展, 2001, 13(05): 351-.
阅读次数
全文


摘要

手性亚砜合成*