Diels-alder reaction of the N-protected 3-phenylthio-2 (1H)-dihydropyridinone derivatives

Y Torisawa, M Nakagawa, H Takami, T Nagata, MA Ali…

Index: Torisawa, Yasuhiro; Nakagawa, Masako; Takami, Hideo; Nagata, Toshiaki; Ali, Mohamed Ayman; et al. Heterocycles, 1994 , vol. 39, # 1 p. 277 - 292

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Citation Number: 12

Abstract

Efficient methods for the preparation of N-protected 3-phenylthio-2 (1H)-dihydropyridinones from 2-piperidone and their Diels-Alder reaction with 2-trimetylsilyloxybutadiene are described. The role of the electron-withdrawing N-protecting group in the dienophiles is rationalized in terms of the lowered energy level in LUMO.