Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 24, Pages 14861-14881Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01320
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Funding
- University of Rennes 1
- Centre National de la Recherche Scientifique (CNRS)
- Ministerio de Economia y Competitividad (MINECO) of Spain
- FEDER [CTQ2016-80375-P, CTQ2014-51912-REDC]
- Gobierno Vasco/Eusko Jaurlaritza (GV/EJ) [IT-324-07]
- La region Bretagne
- Eusko Jaurlaritza-Gobierno Vasco
- VillaPharma Research
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An unexpected 1,3-dioxa-[3,3]-sigmatropic rearrangement during the treatment of aryl- and alkenyl-substituted allylic alcohols with activated isocyanates is reported. The reorganization of bonds is highly dependent on the electron density of the aromatic ring and the nature of isocyanate used. This metal-free tandem reaction from branched allyl alcohols initiated by a carbamoylation reaction and followed by a sigmatropic rearrangement thus offers a new access to (E)-cinnamyl and conjugated (E,E)-diene carbamates, such as N-acyl and N-sulfonyl derivatives. A computational study was conducted in order to rationalize this phenomenon, and a rearrangement progress kinetic analysis was performed.
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