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Catalytic asymmetric multiple dearomatizations of phenols enabled by a cascade 1,8-addition and Diels-Alder reaction.

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.

SUBMITTER: Liu X

PROVIDER: S-EPMC8146773 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Catalytic asymmetric multiple dearomatizations of phenols enabled by a cascade 1,8-addition and Diels-Alder reaction.

Liu Xihong X Zhang Jingying J Bai Lutao L Wang Linqing L Yang Dongxu D Wang Rui R

Chemical science 20191206 3

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 <i>para</i>-quinone methides generated <i>in situ</i> from propargylic alcohols and a subsequent intramolecular dearomative Diels-Alder reaction. Notewort ...[more]

PMID: 34123039

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