Abstract
Electron transfer-initiated photocyclizations of the title compounds [ ( Z)- 1 ] with an ( S)-alanine methyl ester auxiliary in methanol containing a tertiary amine were found to give ( S, S)- and ( R, S)-3,4-dihydrobenzo[ f]quinolinones ( 2 ) as major products. The magnitude of diastereomeric excess (de) for ( S, S)- 2 was varied from 0 to 55%, depending on the properties of the amine and solvent employed. The mechanism of asymmetric induction in the photocyclization process eventually affording 2 was discussed based on solvent, tertiary amine and temperature effects on the de value.
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