Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Note | Regular issue | Vol 81, No. 4, 2010, pp.997-1006
Published online, 29th January, 2010
DOI: 10.3987/COM-10-11911
■ Photoinduced Electron Transfer-Initiated Selective Cyclization Reactions of (Z)-N-Benzoyl-α-dehydro(1-naphthyl)alaninamides into 4,5-Dihydrooxazole Derivatives

Yuhki Sato, Atsuhiko Yoshida, Tetsutaro Igarashi, and Tadamitsu Sakurai*

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

Abstract

An investigation was undertaken to gain understanding of substituent and solvent effects on the photoreactivity of the title 1-naphthylalanine N’,N’-disubstituted amides [(Z)-1] and the (Z)-1-derived product composition. Results indicated that the photoinduced electron transfer reaction of (Z)-1 in methanol containing triethylamine (TEA) proceeds less efficiently than that of the corresponding 1-naphthylalanine alkyl esters to afford cis-4,5-dihydrooxazoles in preference to the trans-isomers and also the former isomers undergo negligible isomerization to the latter isomers in the presence of TEA. Analysis of solvent effects substantiated that both the polarity of solvent and the ability of solvent to donate proton or to accept electron are major factors for controlling the photoreactivity and product composition ratio.