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Updated: Jul 9, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Enantioselective, organocatalytic oxy-michael addition to gamma/delta-hydroxy-alpha,beta-enones: boronate-amine
De Run Li1, Andiappan Murugan, J R Falck
1Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390.
Abstract:
An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha,beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
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