Metal-Free Enantioselective 1,4-Addition of Diarylphosphine Oxides to α,β-Unsaturated Carboxylic Esters

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7573 - 7578

Published: May 23, 2024

The catalytic asymmetric conjugate addition of phosphorus nucleophiles to unsaturated compounds, catalyzed by metallic or nonmetallic catalysts, has been extensively developed. However, the enantioselective transformations involving α,β-unsaturated carboxylic esters for constructing chiral c-p bonds have rarely reported, particularly in metal-free processes. In this study, we present a novel methodology 1,4-addition diarylphosphine oxides using classical oxazaborolidine catalysts. Remarkably high yields and enantioselectivities were obtained most products. Furthermore, these valuable serve as crucial intermediates that can be transformed into various derivatives including amides, acids, alcohols single step.

Language: Английский

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Enantioselective C−C Bond Insertion into Aldehydes via Oxazaborolidinium Catalyzed 1,2-Acyl Shift

Synfacts, Journal Year: 2024, Volume and Issue: 20(03), P. 0300 - 0300

Published: Feb. 14, 2024

Key words COBI-catalyst - C–C bond insertion all-carbon quaternary stereocenters

Language: Английский

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Remote enantioselective desymmetrization of cyclohexanone with carbonyl 1,2-transposition

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(4), P. 100974 - 100974

Published: April 1, 2024

Language: Английский

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