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Paper | Special issue | Vol 76, No. 1, 2008, pp.267-273
Published online, 25th January, 2008
DOI: 10.3987/COM-07-11296
Cycloaddition of 2-Pyridones Having an Electron-Withdrawing Group

Masato Hoshino, Hisao Matsuzaki, and Reiko Fujita*

*Tohoku Pharmaceutical University, 4-4-1, Komatsushima, Aoba-ku, Sendai, Miyagi 981-8558, Japan


Cycloaddition of 1-methyl-2(1H)-pyridones bearing an electron-withdrawing group at 3-5 positions acting as the diene with N-phenylmaleimide was carried out under atmospheric and high pressure conditions to give the corres-ponding isoquinuclidines. Stereoselectivity of the cycloaddition of 1-methyl-2(1H)-pyridones was investigated using molecular orbital calculations.