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Communication | Special issue | Vol 74, No. 1, 2007, pp.149-157
Published online, 21st September, 2007
DOI: 10.3987/COM-07-S(W)24
Photoinduced Electron Transfer-Initiated Enantioselective Cyclization of N-Benzoyl-α-dehydroarylalanine tert-Butyl Esters in the Presence of Chiral Amine

Haruo Watanabe, Kei Maekawa, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan


The asymmetric photocyclization of the title compounds in 1,2-dichloroethane was found to proceed cleanly in the presence of primary, secondary, or tertiary chiral amine to give the corresponding cis- and trans-3,4-dihydrooxazole derivatives in enantiomeric excess (ee) of 11-38% and 6-33%, respectively, depending on the steric factor of the aryl substituent as well as on the hydrogen-bonding ability of the chiral amine.