Phosphine-Free Suzuki–Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides

Phosphine-Free Suzuki–Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides

A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-α-glycosides and 1,5-anhydro-2-C-aryl-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki–Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with com...

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Veröffentlicht in:Organic letters 2012-04, Vol.14 (7), p.1728-1731
Hauptverfasser: Cobo, Isidro, Matheu, M. Isabel, Castillón, Sergio, Boutureira, Omar, Davis, Benjamin G
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Glycosides - chemical synthesis
Glycosides - chemistry
Molecular Structure
Phosphines
Water
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Zusammenfassung:A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-α-glycosides and 1,5-anhydro-2-C-aryl-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki–Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3003139