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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.

Original publication

DOI

10.1021/ol3003139

Type

Journal article

Journal

Org Lett

Publication Date

06/04/2012

Volume

14

Pages

1728 - 1731

Keywords

Catalysis, Glycosides, Molecular Structure, Phosphines, Water