ArticleOrganic letters2014
Asymmetric synthesis of highly functionalized tetrahydropyrans via a one-pot organocatalytic Michael/Henry/ketalization sequence.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Synthesis of Bicyclic Hemiacetals Catalyzed by Unnatural Densely Substituted γ-Dipeptides.The Journal of organic chemistry · 2022Article
- Crystallization-Enabled Henry Reactions: Stereoconvergent Construction of Fully Substituted [Journal of the American Chemical Society · 2022Article
- Article
- Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry-Hemiaminalization-Oxidation Sequence.Synthesis · 2015Article
- Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction.Organic letters · 2014Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
A diastereo- and enantioselective Michael/Henry/ketalization sequence to functionalized tetrahydropyrans is described. The multicomponent cascade reaction uses acetylacetone or β-keto esters, β-nitrostyrenes, and alkynyl aldehydes as substrates affording tetrahydropyrans with five contiguous stereocenters. Employing a bifunctional quinine-based squaramide organocatalyst, the title compounds are obtained in moderate to good yields (27-80%), excellent enantiomeric excesses (93-99% ee), and high diastereomeric ratios (dr > 20:1) after one crystallization.
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Registered trials
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