4.4 Article

Hafnium(IV) triflate as a highly efficient catalyst for Ferrier rearrangement of O- and S-nucleophiles with glycals

Journal

TETRAHEDRON LETTERS
Volume 57, Issue 25, Pages 2758-2762

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.05.026

Keywords

Hafnium(IV) triflate; 3,4,6-Tri-O-acetyl-D-glucal; Hexa-O-acetyl-n-lactal; Ferrier rearrangement; 2,3-Unsaturated glycosides

Funding

  1. National Natural Science Foundation of China [20332006, 21572105]
  2. Natural Science Foundation of Tianjin [12JCYBJC18600]

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A highly efficient method to afford 2,3-unsaturated glycosides was described. In the presence of Hafnium (IV) triflate, a variety of 2,3-unsaturated-O- and S-glycosides have been obtained by stereoselective glycosylation of 3,4,6-tri-O-acetyl-D-glucal and hexa-O-acetyl-D-lactal with various acceptors in good isolated yields. (C) 2016 Elsevier Ltd. All rights reserved.

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