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- Title
Carbene‐Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones.
- Authors
Lee, Ansoo; Zhu, Joshua L.; Feoktistova, Taisiia; Brueckner, Alexander C.; Cheong, Paul H.‐Y.; Scheidt, Karl A.
- Abstract
A direct decarboxylative strategy for the generation of aza‐o‐quinone methides (aza‐o‐QMs) by N‐heterocyclic carbene (NHC) catalysis has been discovered and explored. This process requires no stoichiometric additives in contrast with current approaches. Aza‐o‐QMs react with trifluoromethyl ketones through a formal [4+2] manifold to access highly enantioenriched dihydrobenzoxazin‐4‐one products, which can be converted to dihydroquinolones through an interesting stereoretentive aza‐Petasis–Ferrier rearrangement sequence. Complementary dispersion‐corrected density functional theory (DFT) studies provided an accurate prediction of the reaction enantioselectivity and lend further insight to the origins of stereocontrol. Additionally, a computed potential energy surface around the major transition structure suggests a concerted asynchronous mechanism for the formal annulation.
- Subjects
CARBENES; ENANTIOSELECTIVE catalysis; QUINOLONE antibacterial agents; STOICHIOMETRIC combustion; DENSITY functional theory
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 18, p6002
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201900600