Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety via a double decarboxylative formal ring-expansion process under palladium catalysis

Direct access to pharmaceutically attractive benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety was achieved a palladium-catalyzed double-decarboxylative formal ring-expansion process from six-membered trifluoromethyl benzo[ ][1,3]oxazinones to nine-membered triflu...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2018-04, Vol.9 (13), p.3276-3281
Main Authors: Das, Pulakesh, Gondo, Satoshi, Nagender, Punna, Uno, Hiroto, Tokunaga, Etsuko, Shibata, Norio
Format: Article
Language:English
Subjects:
Alkenes
Carbonates
Catalysis
Palladium
Transformations
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Summary:Direct access to pharmaceutically attractive benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety was achieved a palladium-catalyzed double-decarboxylative formal ring-expansion process from six-membered trifluoromethyl benzo[ ][1,3]oxazinones to nine-membered trifluoromethyl benzo[ ][1,5]oxazonines in the presence of vinylethylene carbonates . Generation of a Pd-π-allyl zwitterionic intermediate was proposed in the catalytic cycle. The trifluoromethyl group in the benzoxazinanones plays an important role throughout the transformation. Diastereoselective chemical transformations of products were also demonstrated.
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc05447e