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Communication | Regular issue | Vol 57, No. 9, 2002, pp.1591-1597
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9559
Asymmetric Photocyclizations of Chiral Auxiliary-substituted N-Acyl-α-dehydroamino Acids into 1,2-Dihydrobenzoquinolinone Derivatives

Kei Maekawa,* Tetsutaro Igarashi, Kanji Kubo, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering
Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan


The irradiation of the title compounds [(Z)-1] with an (S)-alanine auxiliary in methanol containing a tertiary amine afforded a diastereomeric mixture of (S,S)- and (R,S)-1,2-dihydrobenzo[f]quinolinones, along with (E)-1, benzo[f]isoquinoline, and 1-azetine derivatives. It was found that electron transfer-initiated photocyclizations of (Z)-1 in polar solvents give (S,S)-1,2-dihydrobenzoquinolinones in diastereomeric excess whose value varies from 0 to 55% depending on the properties of the amine and solvent employed.