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Synlett
DOI: 10.1055/s-0043-1773538
DOI: 10.1055/s-0043-1773538
letter
Emerging Trends in Organic Chemistry: A Focus on India
Regioselective Formal (3+2) Cyclization of Propargylic para-Quinone Methides (p-QMs) with β-Keto Carbonyls: Direct Access to (Fused)-Furans
S.Y. is thankful for a University of Hyderabad Institute of Eminence grant (UoH/IoE/RC1/2020/8). A.K. and L.A. are thankful to NFSC and CSIR for their fellowships.
Abstract
We report a calcium(II)-catalyzed, base-promoted, formal (3+2) cyclization of para-quinone methides with 1,3-dicarbonyl derivatives to access furans, dihydrofurans, dihydrobenzofurans, and naphthofurans under solvent-free conditions. The reaction shows good substrate generality and excellent regioselectivity.
Key words
propargylic para-quinone methides - calcium catalysis - furans - pyrans - enols - green chemistrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1773538.
- Supporting Information
Publication History
Received: 24 January 2025
Accepted after revision: 21 March 2025
Article published online:
24 April 2025
© 2025. Thieme. All rights reserved
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For selected examples, see:
For examples, see:
For recent reviews on the chemistry of p-QMs, see:
For selected recent examples on racemic 1,6-addition of p-QMs, see:
For selected catalytic asymmetric 1,6-addition of p-QMs, see:
For 1,6-addition of propargylic p-QMs, see: