Use of a confined space (zeolite) in enantio- and diastereo-selective photoreactions

被引:13
作者
Shailaja, J [1 ]
Sivaguru, J [1 ]
Uppili, S [1 ]
Joy, A [1 ]
Ramamurthy, V [1 ]
机构
[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA
基金
美国国家科学基金会;
关键词
zeolite; enantioselectivity; photoreactions; chiral induction;
D O I
10.1016/S1387-1811(01)00348-1
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The confined spaces of zeolites have been found to be ideal for carrying out enantio- and diastereo-selective photoreactions. Four methods, (chiral inductor, chiral auxiliary, a combination (chiral inductor + chiral auxiliary) and chiral inductor as a reagent) have been explored and all were found to give reasonable chiral induction on several systems. The uniqueness of zeolites as media although established in this study, the factors that control the high chiral induction in zeolite with respect to solution are yet to be established. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:319 / 328
页数:10
相关论文
共 21 条
[1]  
[Anonymous], ADV PHOTOCHEM
[2]   THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY [J].
BUSCHMANN, H ;
SCHARF, HD ;
HOFFMANN, N ;
ESSER, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) :477-515
[3]   Enantio- and diastereodifferentiating cis,trans-photoisomerization of 2β,3β-diphenylcyclopropane-1α-carboxylic acid derivatives in organized media [J].
Cheung, E ;
Chong, KCW ;
Jayaraman, S ;
Ramamurthy, V ;
Scheffer, JR ;
Trotter, J .
ORGANIC LETTERS, 2000, 2 (18) :2801-2804
[4]  
Everitt SRL, 1999, MOL SUPRAM PHOTOCHEM, V3, P71
[5]   The ionic auxiliary concept in solid state organic photochemistry [J].
Gamlin, JN ;
Jones, R ;
Leibovitch, M ;
Patrick, B ;
Scheffer, JR ;
Trotter, J .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (04) :203-209
[6]   ASYMMETRIC PHOTOCHEMICAL-REACTIONS IN SOLUTION [J].
INOUE, Y .
CHEMICAL REVIEWS, 1992, 92 (05) :741-770
[7]   The influence of chiral auxiliaries is enhanced within zeolites [J].
Jayaraman, S ;
Uppili, S ;
Natarajan, A ;
Joy, A ;
Chong, KCW ;
Netherton, MR ;
Zenova, A ;
Scheffer, JR ;
Ramamurthy, V .
TETRAHEDRON LETTERS, 2000, 41 (43) :8231-8235
[8]   Asymmetrically modified zeolite as a medium for enantioselective photoreactions: Reactions from spin forbidden excited states [J].
Joy, A ;
Robbins, RJ ;
Pitchumani, K ;
Ramamurthy, V .
TETRAHEDRON LETTERS, 1997, 38 (51) :8825-8828
[9]  
Joy A, 2000, CHEM-EUR J, V6, P1287, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1287::AID-CHEM1287>3.0.CO
[10]  
2-G