Enantioselective Alkylative Kinetic Resolution of 2‑Oxindole-Derived Enolates Promoted by Bifunctional Phase Transfer Catalysts

The first strategy for bringing about highly enantioselective alkylative enolate kinetic resolutions using a simple phase-transfer protocol via SN2 chemistry has been developed. In the presence of a new squaramide-based quaternized cinchona alkaloid-derived catalyst and aqueous base, benzyl, allyl,...

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Bibliographic Details
Published in:Organic letters 2016-10, Vol.18 (20), p.5204-5207
Main Authors: Sorrentino, Emiliano, Connon, Stephen J
Format: Article
Language:English
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Summary:The first strategy for bringing about highly enantioselective alkylative enolate kinetic resolutions using a simple phase-transfer protocol via SN2 chemistry has been developed. In the presence of a new squaramide-based quaternized cinchona alkaloid-derived catalyst and aqueous base, benzyl, allyl, and propargyl halides react with racemic substituted oxindoles to generate densely functionalized products with the two contiguous stereocenters, one of which is an all-carbon quaternary.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02398