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Enantioselective 1,6-Addition of β-Ketoester Enolates to In Situ Generated para-Quinone Methides Enabled by Cooperative Palladium and Brønsted Acid Catalysis.

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We report herein an asymmetric cooperative process for the enantioselective 1,6-addition of β-ketoesters to in situ generated para-quinone methides with chiral Pd-aqua complexes as mixed Brønsted acid-base catalysts. Excellent yields,… Click to show full abstract

We report herein an asymmetric cooperative process for the enantioselective 1,6-addition of β-ketoesters to in situ generated para-quinone methides with chiral Pd-aqua complexes as mixed Brønsted acid-base catalysts. Excellent yields, outstanding enantiocontrol, and good diastereoselectivity across a broad substrate range are highlights of this transformation. The utility of this reaction is further demonstrated by a facile scale up and subsequent complexity-increasing modifications.

Keywords: situ generated; generated para; para quinone; quinone methides; nsted acid; enantioselective addition

Journal Title: Organic letters
Year Published: 2023

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