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Iron(III) chloride-catalysed direct nucleophilic alpha-substitution of Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl compounds, and thiols

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 7, Issue 20, Pages 4186-4193

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/b908447a

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Funding

  1. Nanyang Technological University [RG134/06]

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A general and efficient direct method for the alpha-substitution of Morita-Baylis-Hillman alcohols with carbon-and heteroatom-centred nucleophiles such as alcohols, arenes, 1,3-dicarbonyl compounds, and thiols in the presence of FeCl3 center dot 6H(2)O as catalyst has been developed. The reaction is operationally straightforward, accomplished in good to excellent product yields (40-99%) and with exclusive alpha-regioselectivity under mild conditions that did not need an inert and moisture-free environment.

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