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|Title:||Enhanced diastereoselectivity via confinement: Photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites|
Induced Asymmetric Synthesis
|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.|
|Appears in Collections:||Article|
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