Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O‐Glycosylation of 1‐O‐Acetyl Sugars as Glycosyl Donors. Issue 25 (24th July 2014)

• Record Type: Journal Article
• Authors: Roy, Rashmi; Rajasekaran, Parasuraman; Mallick, Asadulla; Vankar, Yashwant D.
• Is Part Of: European journal of organic chemistry. Issue 25(2014)
• Page Start: 5564
• Page End: 5573
• Publication Date: 2014-07-24
• Subjects: Synthetic methods -- Homogeneous catalysis -- Gold -- Carbohydrates -- Glycosylation -- Rearrangement; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402606
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: We have developed a new catalyst system comprising AuCl3 and phenylacetylene that promotes the Ferrier rearrangement of glycals and 2‐acetoxymethylglycals with different nucleophiles, and also the O ‐glycosylation of 1‐ O ‐acetyl sugars to obtain a variety of useful glycosides at room temperature through relay catalysis. Good anomeric selectivity was observed for the Ferrier rearrangements, whereas the O ‐glycosylation of 1‐ O ‐acetyl sugars gave mixtures of diastereomers with moderate to excellent selectivity. Abstract : The Ferrier rearrangement of glycals, and the glycosylation of 1‐ O ‐acetyl sugars using an AuCl3 /phenylacetylene catalyst system are described. Relay catalysis was observed when phenylacetylene was used in combination with AuCl3 . The efficient production of glycosides was achieved in shortened reaction times.