Carbene-­Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones

Title
Carbene-­Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones
Authors
이안수Joshua L. ZhuTaisiia FeoktistovaAlexander C. BruecknerPaul H.-Y. CheongKarl A. Scheidt
Issue Date
2019-04
Publisher
Angewandte Chemie international edition
Citation
VOL 58, NO 18-5945
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.
URI
http://pubs.kist.re.kr/handle/201004/70413
ISSN
1433-7851
Appears in Collections:
KIST Publication > Article
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