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A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation-Ring-Expansion Approach to Substituted Azepanes

Scott M. Thullen, David M. Rubush, Tomislav Rovis*

*Department of Chemistry, Columbia University, New York, NY 10027, USA, Email: tr2504columbia.edu

S. M. Thullen, D. M. Rubush, T. Rovis, Synlett, 2017, 28, 2755-2758.

DOI: 10.1055/s-0036-1589049 (free Supporting Information)


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Abstract

A photochemical rearrangement of N-vinylpyrrolidinones provides azepin-4-ones in good yields. This transformation allows for the conversion of readily available  pyrrolidinones and aldehydes to densely functionalized azepane derivatives in a facile two-step procedure.

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proposed mechanism



Key Words

azepanes, N-heterocycles, photochemistry, photo-Fries rearrangement, [5+2] cycloaddition


ID: J60-Y2017