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Synlett 2001; 2001(3): 0427-0429
DOI: 10.1055/s-2001-11387
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Highly Stereoselective Synthesis of Pseudoglycals via Yb(OTf)3 Catalyzed Ferrier Glycosylation

Mohamed Takhi* , Adel A.-H. Abdel-Rahman, Richard R. Schmidt
  • *Department of Chemistry, University of Konstanz, 78457 Konstanz, Germany; Fax + 49-75 31-88-31 35; E-mail: rrs@gd3.chemie.uni-konstanz.de
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Publication Date:
31 December 2001 (online)

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The reaction of tri-O-acetyl-d-glucal with various alcohols and thiols was effectively promoted by a catalytic amount of Yb(OTf)3 to produce a variety of pseudoglycals via Ferrier rearrangement in excellent yields and anomeric selectivity.

glycal - pseudoglycal - glycosidation - ytterbium triflate - Ferrier rearrangement