English
新闻公告
More
化学进展 2004, Vol. 16 Issue (03): 386- 前一篇   后一篇

• 综述与评论 •

微反应器中的不对称光化学反应*

马磊;陈彬;吴骊珠**;彭明丽;张丽萍;佟振合**   

  1. (中国科学院理化技术研究所 北京 100101)
  • 收稿日期:2002-12-01 修回日期:2004-01-01 出版日期:2004-05-24 发布日期:2004-05-24
  • 通讯作者: 吴骊珠;佟振合

Asymmetric Photochemical Reactions Conducted within Microreactors

Ma Lei;Chen Bin;Wu Lizhu**;Peng Mingli;Zhang Liping;Tung Chenho**   

  1. (Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101, China)
  • Received:2002-12-01 Revised:2004-01-01 Online:2004-05-24 Published:2004-05-24
  • Contact: Wu Lizhu;Tung Chenho
化学反应的手性诱导一直备受化学家的关注,虽然不对称热化学合成和手性技术已经取得了巨大的进展,但不对称光化学反应的研究远远没有取得相应的成功.激发态寿命短、活化能低是导致其对映选择性低的主要原因.最新的研究表明,采用含手性空间或经手性修饰的微环境可以使光化学反应的立体选择性大大提高.本文针对这一热点问题,综述在微反应器中进行不对称光化学反应的研究进展.
Enantioselectivity of chemical reactions continues to be one of the main concerns of chemists. While many elegant and efficient chiral induction strategies have been developed for a variety of thermal reactions, there are considerably fewer examples of asymmetric induction in photochemical transformations. Short excited state lifetime and low activation energy for reactions in the excited states leave little room for manipulating the diastereomeric transition state when the photochemical reactions occur in solution. The latest progress of asymmetric photochemical reactions revealed that the enantioselectivity in photochemical reactions could be achieved when the reactions take place in chiral environ-ments, which will be reviewed in this article.

中图分类号: 

()

[1] Avalos M, Babino R , Cintas P , et al . Chem. Rev. , 1998 , 98 :2391 —2404
[2] Everitt S R L , Inoue Y. Molecular and Supramolecular Photochemistry. New York : Marcell Dekker , 1999 , Vol . 3 , Chapter 2
[3] Inoue Y, Yamaki N , Yokoyama T A. J . Org. Chem. , 1992 , 57 :1332 —1345
[4] Scheffer J R , Pokkuluri P R. Photochemistry in Organized and Constrained Media ( ed. Ramamurthy V) . New York : VCH ,1991 , Chapter 5
[5] Joy A , Uppili S , Netherton M R , et al . J . Am. Chem. Soc. ,2000 , 122 : 728 —729
[6] Tazuke S , Miyamoto Y. Chem. Lett . , 1986 : 953 —956
[7] Weiss R G. Photochemistry in Organized and Constrained Media (ed. Ramamurthy V) . New York : VCH , 1991 , Chapter 14
[8] Koshima H , Chisaka Y, Wang Y, et al . Tetrahedron , 1994 , 50 :13617 —13630
[9] Gudmundsdttir A D , Scheffer J R. Tetrahedron Lett . , 1990 , 31 :6807 —6810
[10] Chen J , Scheffer J R , Trotter J . Tetrahedron , 1992 , 48 : 3251 —3274
[11] Jones R , Scheffer J R , Trotter J , et al . Tetrahedron Lett . , 1992 ,33 : 5481 —5484
[12] Jones R , Scheffer J R , Trotter J , et al . Acta Crystallogr. , 1994 ,B50 : 601 —607
[13] Leibovitch M, Olovsson G, Scheffer J R. Pure &Appl . Chem. ,1997 , 69 : 815 —823
[14] Toda F , Miyamoto H , Kikuchi S. J . Chem. Soc. , Chem. Commun. , 1995 : 621 —622
[15] Toda F , Akagi K. Tetrahedron Lett . , 1968 : 3965 —3968
[16] Toda F , Ward D L , Hart H. Tetrahedron Lett . , 1981 , 22 :3865 —3868
[17] Toda F , Tanaka K. Chem. Lett . , 1986 : 109 —112
[18] Toda F. Top. Curr. Chem. , 1987 , 140 : 43 —69
[19] Toda F , Tanaka K, Omata T, et al . J . Am. Chem. Soc. , 1983 ,105 : 5151 —5152
[20] Toda F , Tanaka K, Hamai K. Tetrahedron Lett . , 1988 , 29 :551 —554
[21] Bourne S A , Caira M R , Nassimbeni L R. J . Chem. Soc. , Perkin Trans. 2 , 1994 , 1899 —1900
[22] Lutz R E , Jordon R H. J . Am. Chem. Soc. , 1950 , 72 : 4090 —4091
[23] Stobbe H , Bremer K. J . Prakt . Chem. , 1929 , 123 :1 —60
[24] Ohkura K, Kashino S , Haisa M. Bull . Chem. Soc. Jpn. , 1973 ,46 : 627 —628
[25] Schmidt G M J . Pure &Appl . Chem. , 1971 , 27 : 647 —678
[26] Tanaka K, Toda F. J . Chem. Soc. , Chem. Commun. , 1983 :593 —594
[27] Kaftory M, Tanaka K, Toda F. J . Org. Chem. , 1985 , 50 :2154 —2158
[28] Toda F. Top. Curr. Chem. , 1988 , 149 : 211 —238
[29] Tanaka K, Kakinoki O , Toda F. J . Chem. Soc. , Perkin Trans.2 , 1992 , 307 —308
[30] Tanaka K, Toda F. J . Chem. Soc. , Perkin Trans. 1 , 1992 ,943 —944
[31] Toda F , Tanaka K, Yagi M. Tetrahedron , 1987 , 43 : 1495 —1502
[32] Kaftory M, Yagi M, Tanaka K, et al . J . Org. Chem. , 1988 ,53 : 4391 —4393
[33] Toda F , Tanaka K. Tetrahedron Lett . , 1988 , 29 : 4299 —4302
[34] Fyjiwara T, Tanaka N , Tanaka K, et al . J . Chem. Soc. , Perkin Trans. 1 , 1989 , 663 —664
[35] Toda F , Tanaka K. Chem. Lett . , 1987 , 2283 —2284
[36] Tanaka K, Kakinoki O , Toda F. J . Chem. Soc. , Chem. Commun. , 1992 , 1053 —1054
[37] Toda F , Tanaka K, Kakinoki O , et al . J . Org. Chem. , 1993 ,53 : 3783 —3784
[38] Toda F , Miyamoto H , Takeda K, et al . J . Org. Chem. , 1993 ,58 : 6208 —6211
[39] Inoue Y, Wada T, Sugahara N , et al . J . Org. Chem. , 2000 ,65 : 8041 —8050
[40] Nakamura A , Inoue Y. J . Am. Chem. Soc. , 2002 , 125 : 966 —972
[41] Sundarababu M, Leibovitch M, Corbin D R , et al . Chem. Commun. , 1996 , 2159 —2160
[42] Joy A , Robbins R J , Pitchumani K, et al . Tetrahedron Lett . ,1997 , 38 : 8825 —8828
[43] Sivaguru J , Natarajan A , Kaanumalle L A , et al . Acc. Chem.Res. , 2003 , 36 :509 —521
[44] Leibovitch G, Olovsson G, Sundarabaru G, et al . J . Am. Chem.Soc. , 1996 , 118 : 1219 —1220
[45] Arunkumar N , Wang K, Ramamurthy V , et al . Org. Lett . ,2002 , 4 :1443 —1446
[46] Arunkumar N , Joy A , Kaanumalle L S , et al . J . Org. Chem. ,2002 , 67 :8339 —8350
[47] Cheung E , Chong K C W, Jayaraman S , et al . Org. Lett . ,2000 , 2 :2801 —2804
[48] Chong K W, Sivaguru J , Shichi T, et al . J . Am. Chem. Soc. ,2002 , 124 : 2858 —2859
[49] Sivaguru J , Shichi T, Ramamurthy V , et al . Org. Lett . , 2002 ,4 :4221 —4224
[50] Kaanumalle L S , Sivaguru J , Lakshminarasimhan P H , et al . J .Org. Chem. , 2002 , 67 :8711 —8720
[51] Joy A , Scheffer J R , Ramamurthy V. Org. Lett . , 2000 , 2 :119 —121
[52] Joy A , Ramamurthy V. Chem. Eur. J . , 2000 , 6 : 1287 —1293
[53] Sundararajan U , Ramamurthy V. Org. Lett . , 2002 , 4 : 87 —90
[54] Ma L , Wu L Z, Zhang L P , Tung C H. Chin. J . Chem. , 2003 ,21 : 96 —97

[1] 李晓光, 庞祥龙. 液体橡皮泥:属性特征、制备策略及应用探索[J]. 化学进展, 2022, 34(8): 1760-1771.
[2] 赵婉茹, 胡欣, 朱宁, 方正, 郭凯. 连续流离子聚合[J]. 化学进展, 2018, 30(9): 1330-1340.
[3] 申刚义, 于婉婷, 刘美蓉, 崔勋. 固定化酶微反应器的制备及应用[J]. 化学进展, 2013, 25(07): 1198-1207.
[4] 梁振鹏,王朝阳,孙启龙,童真. LbL层层纳米自组装法制备新型微胶囊*[J]. 化学进展, 2004, 16(04): 485-.
阅读次数
全文


摘要

微反应器中的不对称光化学反应*