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Short Paper | Regular issue | Vol 87, No. 6, 2013, pp.1337-1347
Published online, 8th May, 2013
DOI: 10.3987/COM-13-12724
Asymmetric Conversion of (Z)-N-Benzoyl-α-dehydro(9-phenanthryl)alanine -Methylamide into Its Cyclization Intermediates via Photoinduced Electron Transfer

Shin-ichi Matsuki, Takayuki Kimura, Shinsaku Hattori, Kaoru Kawai, Tetsutaro Igarashi, and Tadamitsu Sakurai*

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


Irradiation of (Z)-N-benzoyl-α-dehydro(9-phenanthryl)alanine N´-methylamide [(Z)-1] in 2-propanol-methanol (4:1 v/v) containing (S)-nicotine afforded the (3S,8aS)-3,8a-dihydro-2-dibenzo[f,h]-quinolinone derivative [(3S,8aS)-2] and (3R,8aS)-2 in 20% and 35% enantiomeric excess (ee), respectively. Analysis of the effects of a chiral amine and solvent on the electron transfer-initiated enantioselective photocyclization of (Z)-1 revealed that the magnitude of the ee is predominantly determined by the ability of this amine to form hydrogen bonds at the two sites of the enol intermediate as the precursor of 2.