Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction

The asymmetric domino reaction of various α,α‐dicyano olefins to 3‐nitro‐2H‐chromenes was studied employing readily available cinchona‐derived bifunctional thioureas as organocatalysts. These new transformations were highly regio‐, chemo‐, diastereo‐, and enantioselective simultaneously giving chira...

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Veröffentlicht in:European journal of organic chemistry 2012-12, Vol.2012 (35), p.6924-6932
Hauptverfasser: Guo, Zhi-Wei, Li, Xin-Sheng, Zhu, Wei-Dong, Xie, Jian-Wu
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Sprache:eng
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Zusammenfassung:The asymmetric domino reaction of various α,α‐dicyano olefins to 3‐nitro‐2H‐chromenes was studied employing readily available cinchona‐derived bifunctional thioureas as organocatalysts. These new transformations were highly regio‐, chemo‐, diastereo‐, and enantioselective simultaneously giving chiral multi‐functionalized polyheterocyclic benzopyran derivatives with multi‐chiral carbon centers. Chiral multi‐functionalized polyheterocyclic benzopyran derivatives were easily obtained with excellent diastereoselectivities and good‐to‐excellent enantioselectivities from electron‐deficient α,α‐dicyano olefins and 3‐nitro‐2H‐chromene derivatives under mild and simple conditions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200928