N-heterocyclic carbene-catalyzed enantioselective synthesis of spirocyclic ketones bearing gem-difluoromethylenes?
Organic Chemistry Frontiers Pub Date: 2023-05-15 DOI: 10.1039/D3QO00503H
Abstract
An enantioselective construction of spirocyclic ketones featuring stereogenic carbon centers bearing the gem-difluoromethylene group has been accomplished through N-heterocyclic carbene (NHC)-catalyzed umpolung [3 + 2] annulation of enals with cyclic gem-difluoroalkyl ketones. The structure of the NHC precatalyst and the reaction temperature were found to be the key parameters for the success of this reaction. This protocol offers an alternative pathway to access a new class of structurally interesting cyclic chiral gem-difluoromethylenes, which might be potentially useful in synthetic and medicinal chemistry.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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