A nickel(ii)-catalyzed enantioselective all-carbon-based inverse-electron-demand Diels–Alder reaction of 2-pyrones with indenes. Issue 15 (17th June 2022)

• Record Type: Journal Article
• Authors: Zhang, Fangqing; Ren, Bing-Tao; Liu, Yangbin; Feng, Xiaoming
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 15(2022)
• Page Start: 3956
• Page End: 3960
• Publication Date: 2022-06-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00493c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An asymmetric IEDDA reaction of 2-pyrones with indenes catalyzed by a chiral N, N ′-dioxide/Ni(OTf)2 complex has been disclosed to construct highly functionalized hexahydrofluorenyl bridged-lactone scaffolds in high yields and ee. 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.