Intramolecular [4+ 4] photocycloaddition of 2-pyridones tethered by a three-carbon chain: studies on the formation of cycloadducts and control of stereogenesis. 3

SM Sieburth, G Hiel, CH Lin…

Index: Sieburth, Scott McN.; Hiel, Gary; Lin, Chao-Hsiung; Kuan, Dora P. Journal of Organic Chemistry, 1994 , vol. 59, # 1 p. 80 - 87

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Citation Number: 31

Abstract

Irradiation of a pair of 2-pyridonestethered at the 3-and 6'-positions by a three-carbon chain initiates an efficient 14+ 41 cycloaddition to produce a densely functionalized, fused 5-8 carbocyclic ring system with the trans isomer predominant. An asymmetric center on the tether influences stereogenesis at the four new tetrahedral centers. This effect was probed with an alcohol substituent and its silyl ether as a function of solvent. A combination of ...