Transition-Metal-Free Reactions of Boronic Acids: 1,3-Stereochemical Induction in the Substrate-Controlled Conjugate Addition

The substrate-controlled 1,3-stereoselective conjugate addition of boronic acids and potassium trifluoroborates under metal-free conditions has been developed. This reaction affords bicyclic acetals, which have been used as key intermediates in the stereodivergent synthesis of polysubstituted tetrah...

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Veröffentlicht in:Journal of organic chemistry 2013-12, Vol.78 (24), p.12825-12830
Hauptverfasser: Roscales, Silvia, Ortega, Víctor, Csákÿ, Aurelio G
Format: Artikel
Sprache:eng
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Zusammenfassung:The substrate-controlled 1,3-stereoselective conjugate addition of boronic acids and potassium trifluoroborates under metal-free conditions has been developed. This reaction affords bicyclic acetals, which have been used as key intermediates in the stereodivergent synthesis of polysubstituted tetrahydropyrans.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402262m