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Asymmetric Cycloaddition Reactions of Oxindole α-Keto Esters via Cascade Dienamine-Enamine and Trienamine Strategies
Subramaniam Muthusamy,
Published in Wiley-VCH Verlag
Volume: 2019
Issue: 25
Pages: 4046 - 4055
An asymmetric [3 + 2] formal cycloaddition reaction between oxindole α-keto esters and enals has been developed. This α,γ-regioselective reaction afforded multifunctional carbocyclic oxindoles via dienamine-enamine cascade reaction followed by isomerization. Furthermore, a highly enantioselective Diels-Alder reaction was demonstrated between 2,4-dienals and oxindole α-keto esters via trienamine intermediates. Chiral secondary amine catalyzed the both reactions under mild conditions and the cyclized products were isolated in moderate to good yields with good diastereoselectivities (>20:1 dr) and enantioselectivities (up to 99 %). © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
About the journal
JournalData powered by TypesetEuropean Journal of Organic Chemistry
PublisherData powered by TypesetWiley-VCH Verlag
Open AccessNo