N‐Heterocyclic Carbene‐Catalyzed Enantioselective Intramolecular Annulations to Construct Benzo‐Fused Pyranones with Quaternary Stereocenter

N‐Heterocyclic Carbene‐Catalyzed Enantioselective Intramolecular Annulations to Construct Benzo‐Fused Pyranones with Quaternary Stereocenter

A highly enantioselective intramolecular NHC‐catalyzed approach for the synthesis of benzo‐fused pyranones bearing quaternary stereocenter is described. The developed methodology is based on annulation reaction between acyl anion intermediates and β,β‐disubstituted Michael acceptors. The reaction of...

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Bibliographic Details
Published in:Advanced synthesis & catalysis Vol. 362; no. 18; pp. 3830 - 3835
Main Authors: Dzieszkowski, Krzysztof, Rafiński, Zbigniew
Format: Journal Article
Language:English
Published: Heidelberg Wiley Subscription Services, Inc 21-09-2020
Subjects:
Chemical reactions
Chemical synthesis
Enantiomers
N-heterocyclic carbene
Organocatalysis
Stereoselectivity
Stetter reaction
Umpolung
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Summary:A highly enantioselective intramolecular NHC‐catalyzed approach for the synthesis of benzo‐fused pyranones bearing quaternary stereocenter is described. The developed methodology is based on annulation reaction between acyl anion intermediates and β,β‐disubstituted Michael acceptors. The reaction offers streamlined and effective access to target products in a highly stereoselective manner.
Bibliography:Birthday.
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Dedication to Professor Grzegorz Mlostoń on the Occasion of his 70
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000550