Journal
CHEMICAL SCIENCE
Volume 9, Issue 13, Pages 3276-3281Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc05447e
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Funding
- JSPS KAKENHI [JP 16H01142]
- Advanced Catalytic Transformation (ACT-C) from the JST Agency [JPMJCR12Z7]
- Grants-in-Aid for Scientific Research [16H01142] Funding Source: KAKEN
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Direct access to pharmaceutically attractive benzo-fused nine-membered heterocyclic alkenes 3 with a trifluoromethyl carbinol moiety was achieved via a palladium-catalyzed double-decarboxylative formal ring-expansion process from six-membered trifluoromethyl benzo[d][1,3]oxazinones 1 to nine-membered trifluoromethyl benzo[c][1,5]oxazonines 3 in the presence of vinylethylene carbonates 2. Generation of a Pd-p-allyl zwitterionic intermediate was proposed in the catalytic cycle. The trifluoromethyl group in the benzoxazinanones 1 plays an important role throughout the transformation. Diastereoselective chemical transformations of products 3 were also demonstrated.
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