Brnsted acid-catalysed desilylative heterocyclisation to form substituted furans

Heterocyclisation of tert -butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by para -toluenesulfonic acid ( p -TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to give a range of furan products (21...

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Published in:Organic & biomolecular chemistry 2022-12, Vol.21 (1), p.163-168
Main Authors: Babcock, Emily G, Rahman, Md. Shafiqur, Taylor, James E
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Summary:Heterocyclisation of tert -butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by para -toluenesulfonic acid ( p -TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to give a range of furan products (21 examples, up to 98% yield). Mechanistic experiments suggest the reaction proceeds via in situ deprotection followed by catalytic dehydrative heterocyclisation. A new catalytic dehydrative heterocyclisation to form mono-, di-, and tri-substituted furans under mild conditions.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01828d