Elsevier

Tetrahedron Letters

Volume 57, Issue 20, 18 May 2016, Pages 2171-2174
Tetrahedron Letters

Highly efficient synthesis of tetrasubstituted 2,3-dihydropyrans by three-component ‘one-pot’ reaction

https://doi.org/10.1016/j.tetlet.2016.04.008Get rights and content

Highlights

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    Highly efficient three-component ‘one-pot’ sequential reaction.

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    Very mild reaction conditions, very simple operation procedure.

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    Wide substrate scope.

Abstract

With ammonium acetate as catalyst, three-component ‘one-pot’ reaction of β-keto perfluoroalkanesulfones, aldehydes, and vinyl ethers proceeded smoothly and afforded tetrasubstituted 2,3-dihydropyrans in moderate to excellent yields. Both aromatic and aliphatic aldehydes, as well as cyclic vinyl ether are compatible with this methodology. All dihydropyran products were obtained as cis- and trans-diastereomeric mixtures. The relative configurations were established by comparing the coupling constants of anomeric protons of both isomers and confirmed by single-crystal X-ray diffraction analysis.

Section snippets

Acknowledgment

Support from the National Natural Science Foundation of China (21272257) is gratefully acknowledged.

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