Issue 15, 2022

A nickel(ii)-catalyzed enantioselective all-carbon-based inverse-electron-demand Diels–Alder reaction of 2-pyrones with indenes

Abstract

The Cephalotaxus norditerpenoids cephanolides A–D feature a densely functionalized hexahydrofluorenyl bridged-lactone scaffold. To concisely achieve these privileged structures, herein, an asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction of electron-deficient 2-pyrones with electronically unbiased indenes catalyzed by a chiral N,N′-dioxide/Ni(OTf)2 complex has been disclosed. Based on this reaction, a variety of substituted hexahydrofluorenyl lactone scaffolds were obtained with good to excellent yields (up to 98% yield) and enantioselectivities (up to 93% ee) under mild conditions.

Graphical abstract: A nickel(ii)-catalyzed enantioselective all-carbon-based inverse-electron-demand Diels–Alder reaction of 2-pyrones with indenes

Supplementary files

Article information

Article type
Research Article
Submitted
27 mar 2022
Accepted
08 jun 2022
First published
10 jun 2022

Org. Chem. Front., 2022,9, 3956-3960

A nickel(II)-catalyzed enantioselective all-carbon-based inverse-electron-demand Diels–Alder reaction of 2-pyrones with indenes

F. Zhang, B. Ren, Y. Liu and X. Feng, Org. Chem. Front., 2022, 9, 3956 DOI: 10.1039/D2QO00493C

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