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
[11]   ASYMMETRIC PHOTOCHEMICAL-REACTIONS IN SOLUTION [J].
INOUE, Y .
CHEMICAL REVIEWS, 1992, 92 (05) :741-770
[12]   ENANTIODIFFERENTIATING CIS-TRANS PHOTOISOMERIZATIONS OF 1,2-DIARYLCYCLOPROPANES AND 2,3-DIPHENYLOXIRANE SENSITIZED BY CHIRAL AROMATIC ESTERS [J].
INOUE, Y ;
YAMASAKI, N ;
SHIMOYAMA, H ;
TAI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1785-1793
[13]   Chirally modified zeolites as reaction media: Photochemistry of an achiral tropolone ether [J].
Joy, A ;
Scheffer, JR ;
Ramamurthy, V .
ORGANIC LETTERS, 2000, 2 (02) :119-121
[14]   Photochemistry of a tropolone ether and 2,2-dimethyl-1-(2H)-naphthalenones within a zeolite:: Enhanced diastereoselectivity via confinement [J].
Joy, A ;
Uppili, S ;
Netherton, MR ;
Scheffer, JR ;
Ramamurthy, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (04) :728-729
[15]   Cation-π interaction controlled selective geometric photoisomerization of diphenylcyclopropane [J].
Lakshminarasimhan, P ;
Sunoj, RB ;
Chandrasekhar, J ;
Ramamurthy, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4815-4816
[16]   An investigation of the yang photocyclization reaction in the solid state: Asymmetric induction studies and crystal structure-reactivity relationships [J].
Leibovitch, M ;
Olovsson, G ;
Scheffer, JR ;
Trotter, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12755-12769
[17]  
OUANNES C, 1973, J AM CHEM SOC, V95, P8572
[18]   ASYMMETRIC PHOTOCHEMISTRY IN SOLUTION [J].
RAU, H .
CHEMICAL REVIEWS, 1983, 83 (05) :535-547
[19]   Solid state organic chemistry: Efficient reactions, remarkable yields, and stereoselectivity [J].
Toda, F .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (12) :480-486
[20]   PHOTOCHEMISTRY IN ORGANIZED AND CONFINING MEDIA - A MODEL [J].
WEISS, RG ;
RAMAMURTHY, V ;
HAMMOND, GS .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (10) :530-536