Experimental and Computational Studies of the Diastereoselective Alkylations of 3‑Substituted γ‑Sultams

Experimental and Computational Studies of the Diastereoselective Alkylations of 3‑Substituted γ‑Sultams

We report that chiral 3-substituted γ-sultam α-carbanions undergo diastereoselective alkylation reactions with alkyl halides to predominantly produce trans-3,5-disubstituted γ-sultam products. Quantum mechanical calculations provided a stereoelectronic rationale for the observed diastereoselectivity...

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Veröffentlicht in:Journal of organic chemistry 2015-01, Vol.80 (1), p.685-689
Hauptverfasser: Fauber, Benjamin P, Clagg, Kyle, Gibbons, Paul, René, Olivier
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Crystallography, X-Ray
Models, Molecular
Molecular Conformation
Naphthalenesulfonates - chemical synthesis
Naphthalenesulfonates - chemistry
Quantum Theory
Stereoisomerism
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Zusammenfassung:We report that chiral 3-substituted γ-sultam α-carbanions undergo diastereoselective alkylation reactions with alkyl halides to predominantly produce trans-3,5-disubstituted γ-sultam products. Quantum mechanical calculations provided a stereoelectronic rationale for the observed diastereoselectivity.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502506j