Journal
TETRAHEDRON LETTERS
Volume 53, Issue 46, Pages 6257-6260Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.09.023
Keywords
Sacrificial anode; Zirconium catalyst; Ferrier rearrangement; Hetero-Michael addition; Peracetylated D-glucal; X-ray analysis; Methyl vinyl ketone
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Funding
- Ministry of Education and Science of the Republic of Serbia [172034]
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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. (C) 2012 Elsevier Ltd. All rights reserved.
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