Organic Letters 2012-04-06

Phosphine-free Suzuki-Miyaura cross-coupling in aqueous media enables access to 2-C-aryl-glycosides.

Isidro Cobo, M Isabel Matheu, Sergio Castillón, Omar Boutureira, Benjamin G Davis

Index: Org. Lett. 7th ed., 14 , 1728-1731, (2012)

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Abstract

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.