Anodic generation of a zirconium catalyst for Ferrier rearrangement and hetero Michael addition

• Published in: Tetrahedron letters Vol. 53; no. 46; pp. 6257 - 6260
• Main Authors: Stevanovic, Dragana, Pejovic, Anka, Damljanovic, Ivan, Vukicevic, Mirjana, Bogdanovic, Goran A., Vukicevic, Rastko D.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 14.11.2012; Elsevier
• Subjects: Anodic; Bonding; Carbon-carbon composites; Catalysts; Chemistry; Chemistry, Organic; Conjugates; Ferrier rearrangement; Hetero-Michael addition; Ketones; Methyl vinyl ketone; Michael reaction; Peracetylated d-glucal; Physical Sciences; Sacrificial anode; Science & Technology; Tetrahedrons; X-ray analysis; Zirconium; Zirconium catalyst; Hetero-Michael addition; Methyl vinyl ketone; Zirconium catalyst; Sacrificial anode; X-ray analysis; Peracetylated d-glucal; Ferrier rearrangement; TETRACHLORIDE; ZROCL2-CENTER-DOT-8HO; AZA; GLYCOSYLATION; REDUCTION; AMINES; Peracetylated D-glucal; CONDENSATION; EFFICIENT; CONJUGATE ADDITION; CHLORIDE
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2012.09.023

A zirconium catalyst was successfully generated from a sacrificial anode into the media containing reactants for either a Ferrier rearrangement or a hetero-Michael addition. An efficient catalyst for Ferrier rearrangement and hetero-Michael addition was successfully generated from a sacrificial zirconium anode into media containing reactants for these reactions. Thus, the catalyst generated, successfully promoted the allylic rearrangement of peracetylated d-glucal in the presence of a suitable S-nucleophile, giving the corresponding 2,3-unsaturated d-glucopyranose (pseudoglycal) in good to high yields. This catalyst was also shown to be capable of promoting hetero-Michael conjugate addition of S- and N-nucleophiles to the carbon–carbon double bond of methyl vinyl ketone, resulting in new carbon–sulfur and carbon–nitrogen bond formation.