Sulfoxide-Directed Enantioselective Synthesis of Functionalized Tetrahydropyridines

Sulfoxide-Directed Enantioselective Synthesis of Functionalized Tetrahydropyridines

The highly selective base-promoted cyclization of enantiopure sulfinyl dienamines provides stereodefined sulfinyl 1,2,3,6-tetrahydropyridines (dr up to 99:1). Subsequent sigmatropic rearrangement affords tetrahydropyridin-3-ols in good yields and selectivities.

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Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2013-10, Vol.15 (19), p.4936-4939
Hauptverfasser: Fernández de la Pradilla, Roberto, Simal, Carmen, Bates, Robert H, Viso, Alma, Infantes, Lourdes
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Molecular Structure
Pyridines - chemical synthesis
Pyridines - chemistry
Safrole - analogs & derivatives
Safrole - chemistry
Stereoisomerism
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Zusammenfassung:The highly selective base-promoted cyclization of enantiopure sulfinyl dienamines provides stereodefined sulfinyl 1,2,3,6-tetrahydropyridines (dr up to 99:1). Subsequent sigmatropic rearrangement affords tetrahydropyridin-3-ols in good yields and selectivities.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402141d