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

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 electronic...

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Published inOrganic chemistry frontiers an international journal of organic chemistry Vol. 9; no. 15; pp. 3956 - 3960
Main Authors Zhang, Fangqing, Bing-Tao, Ren, Liu, Yangbin, Feng, Xiaoming
Format Journal Article
LanguageEnglish
Published London Royal Society of Chemistry 26.07.2022
Subjects
Diels-Alder reactions
Electrons
Enantiomers
Nickel
Organic chemistry
Scaffolds
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00493c