The influence of chiral auxiliaries is enhanced within zeolites

被引:25
作者
Jayaraman, S
Uppili, S
Natarajan, A
Joy, A
Chong, KCW
Netherton, MR
Zenova, A
Scheffer, JR
Ramamurthy, V [1 ]
机构
[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA
[2] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
基金
加拿大自然科学与工程研究理事会; 美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(00)01459-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Zeolites significantly enhance the influence of chiral auxiliaries during photochemical reactions. The generality of this phenomenon has been tested with three independent examples. Chiral auxiliaries that lead to 1:1 mixtures of diastereomers in solution give products in up to 80% diastereomeric excess in the presence of faujasite type zeolites. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8231 / 8235
页数:5
相关论文
共 20 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]   Linearly conjugated benzocyclohexadienone photochemistry in the solid state: ionic chiral auxiliary mediated asymmetric induction [J].
Cheung, E ;
Netherton, MR ;
Scheffer, JR ;
Trotter, J .
TETRAHEDRON LETTERS, 1999, 40 (50) :8737-8740
[4]  
CHEUNG E, UNPUB TETRAHEDRON LE
[5]  
Everitt SRL, 1999, MOL SUPRAM PHOTOCHEM, V3, P71
[6]  
FALJONI A, 1974, TETRAHEDRON LETT, V13, P1127
[7]   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
[8]   ASYMMETRIC INDUCTION DURING ENERGY TRANSFER [J].
HAMMOND, GS ;
COLE, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) :3256-&
[9]   ON MECHANISM OF PHOTOISOMERIZATION OF 1(2H)-NAPHTHALENONES [J].
HART, H ;
MURRAY, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (05) :1535-&
[10]  
HORNER L, 1979, LIEBIGS ANN CHEM, P1232