Issue 16, 2024

Brønsted acid-mediated selective α-alkenylation of 3,4-dihydro-2H-pyrans

Abstract

A protocol for the synthesis of α-alkenylated tetrahydropyrans (THPs) with 3,4-dihydro-2H-pyran derivatives and potassium alkenyltrifluoroborates was achieved in the presence of a Brønsted acid and a Lewis acid under mild reaction conditions. The oxonium ion intermediates, produced from various readily available 3,4-dihydro-2H-pyran derivatives, were attacked by the nucleophile to form the desired α-alkenylated products. This strategy could be an alternative approach to modify a series of modules that are of broad utility in natural products and fine chemicals.

Graphical abstract: Brønsted acid-mediated selective α-alkenylation of 3,4-dihydro-2H-pyrans

Supplementary files

Article information

Article type
Research Article
Submitted
24 Mar 2024
Accepted
15 Jun 2024
First published
17 Jun 2024

Org. Chem. Front., 2024,11, 4402-4407

Brønsted acid-mediated selective α-alkenylation of 3,4-dihydro-2H-pyrans

N. Chen, C. Li, S. Liao, J. Chen, X. Ma and Q. Song, Org. Chem. Front., 2024, 11, 4402 DOI: 10.1039/D4QO00541D

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