Highly Regio- and Diastereoselective Synthesis of 6,7-Dihydro‑4H‑furo[3,4‑c]pyran Derivatives through Pd-Catalyzed Formal (3 + 3) Allylic Cycloaddition of 2‑Butene-1,4-diols with 2‑(1-Alkynyl)-2-alken-1-ones

A highly efficient synthesis of 7-vinyl-6,7-dihydro-4H-furo­[3,4-c]­pyran derivatives from 2-butene-1,4-diols and 2-(1-alkynyl)-2-alken-1-ones has been achieved with high regio- and diastereoselectivity (dr > 20:1) by Pd-catalyzed tandem heterocyclization/cross-coupling. The π-allyl palladium spe...

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Bibliographic Details
Published in:Organic letters 2024-03, Vol.26 (10), p.2018-2022
Main Authors: Yao, Tuanli, She, Jun-E, Li, Tao, Qin, Xiangyang
Format: Article
Language:English
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Summary:A highly efficient synthesis of 7-vinyl-6,7-dihydro-4H-furo­[3,4-c]­pyran derivatives from 2-butene-1,4-diols and 2-(1-alkynyl)-2-alken-1-ones has been achieved with high regio- and diastereoselectivity (dr > 20:1) by Pd-catalyzed tandem heterocyclization/cross-coupling. The π-allyl palladium species Int II generated from 2-butene-1,4-diol by direct cleavage of the C–OH bond is the key to the success in this formal (3 + 3) cycloaddition reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00089