Photocycloaddition of four-carbon-tethered pyridones. Intramolecular hydrogen bonding and facilitated amide hydrolysis by a proximal secondary alcohol |
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| Authors: | Zhu Man Qiu Zhilei Hiel Gary P Sieburth Scott McN |
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| Institution: | Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. |
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| Abstract: | 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. |
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