Photocycloaddition of Four-Carbon-Tethered Pyridones. Intramolecular Hydrogen Bonding and Facilitated Amide Hydrolysis by a Proximal Secondary Alcohol1

…, Z Qiu, GP Hiel, SMN Sieburth

文献索引：Zhu, Man; Qiu, Zhilei; Hiel, Gary P.; Sieburth, Scott McN. Journal of Organic Chemistry, 2002 , vol. 67, # 10 p. 3487 - 3493

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被引用次数: 15

摘要

Four-carbon-tethered pyridones undergo photocycloaddition to give exclusively trans-[4+ 4] products. The presence of a tether alcohol engenders a solvent-dependent diastereoselectivity for the cycloaddition by intramolecular hydrogen bonding to the adjacent pyridone. Following cycloaddition, the alcohol can deliver a carbonyl group to the proximal, hindered amide nitrogen, leading to a very facile amide hydrolysis.