A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy Towards Oxazocine Scaffolds

Abstract A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with comple...

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Bibliographic Details
Published in:Synlett 2021-06, Vol.32 (10), p.981-986
Main Authors: Scuiller, Anaïs, Liu, Xueyang, Cordier, Marie, Garrec, Julian, Archambeau, Alexis
Format: Article
Language:English
Subjects:
Chemical Sciences
letter
Organic chemistry
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Summary:Abstract A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1706038