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Enhanced diastereoselectivity via confinement: Photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites

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Title Enhanced diastereoselectivity via confinement: Photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites
 
Creator SIVAGURU, J
SUNOJ, RB
WADA, T
ORIGANE, Y
INOUE, Y
RAMAMURTHY, V
 
Subject 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
 
Description 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.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T01:34:39Z
2011-12-26T12:47:29Z
2011-12-27T05:35:08Z
2011-07-14T01:34:39Z
2011-12-26T12:47:29Z
2011-12-27T05:35:08Z
2004
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 69(20), 6533-6547
0022-3263
http://dx.doi.org/10.1021/jo049365i
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3823
http://hdl.handle.net/10054/3823
 
Language en