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Updated: Nov 2, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Catalytic asymmetric multiple dearomatizations of phenols enabled by a cascade 1,8-addition and Diels-Alder reaction
Xihong Liu1, Jingying Zhang1, Lutao Bai1
1Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University Lanzhou 730000 China yangdx@lzu.edu.cn wangrui@lzu.edu.cn.
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.
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