Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/xmlui/handle/10054/3823
Title: Enhanced diastereoselectivity via confinement: Photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites
Authors: SIVAGURU, J
SUNOJ, RB
WADA, T
ORIGANE, Y
INOUE, Y
RAMAMURTHY, V
Keywords: Circularly Polarized-Light
Induced Asymmetric Synthesis
Cation-Pi Interactions
Gas-Phase
Arylcyclopropane Photochemistry
Rotational Barriers
Optical Yield
Amino-Acids
1,2-Diarylcyclopropanes
N,N-Dimethylformamide
Issue Date: 2004
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY, 69(20), 6533-6547
Abstract: From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding-dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.
URI: http://dx.doi.org/10.1021/jo049365i
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3823
http://hdl.handle.net/10054/3823
ISSN: 0022-3263
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