Catalytic asymmetric multiple dearomatizations of phenols enabled by a cascade 1, 8-addition and Diels–Alder reaction. Issue 3 (9th December 2019)

• Record Type: Journal Article
• Authors: Liu, Xihong; Zhang, Jingying; Bai, Lutao; Wang, Linqing; Yang, Dongxu; Wang, Rui
• Is Part Of: Chemical science. Volume 11:Issue 3(2020)
• Page Start: 671
• Page End: 676
• Publication Date: 2019-12-09
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc05320d
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : The first chiral phosphoric acid catalyzed asymmetric multiple dearomatizations of phenols for the synthesis of bridged polycyclic compounds are reported. Abstract : A direct catalytic asymmetric multiple dearomatization reaction of phenols was disclosed, which provides expedient access to a series of architecturally complex polycyclic compounds bearing four stereogenic centers in high enantiopurity. The key to achieve such a transformation is the combination of a dearomative 1, 8-addition of β-naphthols to para -quinone methides generated in situ from propargylic alcohols and a subsequent intramolecular dearomative Diels–Alder reaction. Noteworthily, this protocol enrichs not only the diversity of dearomatized products but also the toolbox of dearomatization strategies.