Issue 16, 2005

Role of cations and confinement in asymmetric photochemistry: enantio- and diastereo-selective photocyclization of tropolone derivatives within zeolites

Abstract

Asymmetric induction in photochemical reactions has been explored using the photochemistry of tropolones as a model. Three approaches have been examined: chiral inductor, chiral auxiliary and [chiral inductor + chiral auxiliary]. All three methods gave excellent asymmetric induction in zeolite and very little or zero induction in solution. Results presented on tropolones clearly illustrate the remarkable influence that a confined space studded with cations can have on asymmetric induction. Tropolone derivatives, upon irradiation undergo 4π-electron electrocyclization to yield a bicyclic product and a rearranged product. Enantiomeric excess up to 68% has been achieved in the cyclized product. In systems where a chiral inductor has been covalently linked, diastereomeric excess as high as 88% has been achieved within a zeolite while the same system in solution gave 10%.

Graphical abstract: Role of cations and confinement in asymmetric photochemistry: enantio- and diastereo-selective photocyclization of tropolone derivatives within zeolites

Supplementary files

Article information

Article type
Paper
Submitted
07 Apr 2005
Accepted
14 Jun 2005
First published
13 Jul 2005

Org. Biomol. Chem., 2005,3, 3045-3053

Role of cations and confinement in asymmetric photochemistry: enantio- and diastereo-selective photocyclization of tropolone derivatives within zeolites

A. Joy, L. S. Kaanumalle and V. Ramamurthy, Org. Biomol. Chem., 2005, 3, 3045 DOI: 10.1039/B504865F

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