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: tr2504
columbia.edu
S. M. Thullen, D. M. Rubush, T. Rovis, Synlett, 2017, 28, 2755-2758.
DOI: 10.1055/s-0036-1589049
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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
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Key Words
azepanes, N-heterocycles, photochemistry, photo-Fries rearrangement, [5+2] cycloaddition
ID: J60-Y2017
