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

  • Org Lett. 2012 Apr 6;14(7):1728-31. doi: 10.1021/ol3003139.
Isidro Cobo  1 ,  M Isabel Matheu ,  Sergio Castillón ,  Omar Boutureira ,  Benjamin G Davis
Affiliations
  • 1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, UK.
PMID: 22409147 DOI: 10.1021/ol3003139
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.

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