Asymmetric photoreactions within zeolites: Role of confinement and alkali metal ions

被引：167

作者：

Sivaguru, J ^{[1
]}

Natarajan, A ^{[1
]}

Kaanumalle, LS ^{[1
]}

Shailaja, J ^{[1
]}

Uppili, S ^{[1
]}

Joy, A ^{[1
]}

Ramamurthy, V ^{[1
]}

机构：

[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2003年 / 36卷 / 07期

关键词：

D O I：

10.1021/ar020269i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this Account strategies using zeolites as media to achieve chiral induction are presented. Diastereomeric excesses as high as 90% and enantiomeric excesses Lip to 78% have been obtained with selected systems within zeolites. The same systems show no asymmetric induction in solution. Chiral induction is dependent on the alkali ions present in the zeolites. Alkali ions control not only the extent of asymmetric induction but often the isomer being enhanced. Results of ab initio computations have allowed us to gain an insight into the observed selectivity within zeolites.

引用

页码：509 / 521

页数：13

共 40 条

[1] [Anonymous], UNPUB
[2] Arunkumar N, 2002, ORG LETT, V4, P1443
[3] ARUNKUMAR N, 2002, J ORG CHEM, V67, P8339
[4] ARUNKUMAR N, UNPUB
[5] Breck D. W., 1974, ZEOLITE MOL SIEVES S
[6] THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY
BUSCHMANN, H
SCHARF, HD
HOFFMANN, N
ESSER, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) : 477 - 515
[7] Enantio- and diastereodifferentiating cis,trans-photoisomerization of 2β,3β-diphenylcyclopropane-1α-carboxylic acid derivatives in organized media
Cheung, E
Chong, KCW
Jayaraman, S
Ramamurthy, V
Scheffer, JR
Trotter, J
[J]. ORGANIC LETTERS, 2000, 2 (18) : 2801 - 2804
[8] Use of chirally modified zeolites and crystals in photochemical asymmetric synthesis
Chong, KCW
Sivaguru, J
Shichi, T
Yoshimi, Y
Ramamurthy, V
Scheffer, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) : 2858 - 2859
[9] REACTIONS IN CHIRAL CRYSTALS - OPTICALLY-ACTIVE HETEROPHOTODIMER FORMATION FROM CHIRAL SINGLE-CRYSTALS
ELGAVI, A
GREEN, BS
SCHMIDT, GMJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (06) : 2058 - 2059
[10] Everitt SRL, 1999, MOL SUPRAM PHOTOCHEM, V3, P71

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