Enantioselective Annulation of α,β-Unsaturated N‑Acyliminium Ions with β‑Keto Ester Enolates via Cooperative Palladium and Brønsted Acid Catalysis

We herein report a cooperative palladium- and Brønsted acid-catalyzed strategy toward the first enantioselective annulation of in situ generated α,β-unsaturated N-acyliminium ions with chiral metal enolates. Novel polycyclic oxoisoindoles featuring three contiguous stereogenic centers have been obta...

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Bibliographic Details
Published in:Organic letters 2022-05, Vol.24 (19), p.3560-3564
Main Authors: Gärtner, Cornelius V., Schneider, Christoph
Format: Article
Language:English
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Summary:We herein report a cooperative palladium- and Brønsted acid-catalyzed strategy toward the first enantioselective annulation of in situ generated α,β-unsaturated N-acyliminium ions with chiral metal enolates. Novel polycyclic oxoisoindoles featuring three contiguous stereogenic centers have been obtained with typically good yields, outstanding enantiocontrol, and moderate to good diastereoselectivity. The utility of the process was further demonstrated by their conversion to synthetically valuable scaffolds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01265