Issue 5, 2022

Palladium-catalysed diastereodivergent inverse-electron-demand oxa-Diels–Alder reactions of in situ formed cyclopentadienones via ligand-control

Abstract

Here we report Pd(0)-catalysed asymmetric inverse-electron-demand oxa-Diels–Alder reactions between the carbonates of 4-hydroxy-2-cyclopentenones and α-cyano chalcones by in situ generating η2-Pd(0)-cyclopentadienone complexes as HOMO-raised dienophiles, and diastereodivergent synthesis could be realised by employing a bifunctional monophosphine ligand from a chiral aminoalcohol or a proline-derived bisphosphine ligand. More types of α,β-unsaturated carbonyls have also been successfully used as 1-oxadiene partners, furnishing a range of chiral fused dihydropyrans with versatile structural and functional diversity, generally with high stereoselectivity.

Graphical abstract: Palladium-catalysed diastereodivergent inverse-electron-demand oxa-Diels–Alder reactions of in situ formed cyclopentadienones via ligand-control

Supplementary files

Article information

Article type
Research Article
Submitted
17 Dec 2021
Accepted
21 Jan 2022
First published
24 Jan 2022

Org. Chem. Front., 2022,9, 1364-1369

Palladium-catalysed diastereodivergent inverse-electron-demand oxa-Diels–Alder reactions of in situ formed cyclopentadienones via ligand-control

X. Yang, X. Zhao, Q. Ouyang, W. Du and Y. Chen, Org. Chem. Front., 2022, 9, 1364 DOI: 10.1039/D1QO01876K

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