title: Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters.
abstract: Described herein is a general and mild catalytic asymmetric 1,6-conjugate addition of para-quinone methides (p-QMs), a class of challenging reactions with previous limited success. Benefiting from chiral Brønsted acid catalysis, which allows in situ formation of p-QMs, our reaction expands the scope to general p-QMs with various substitution patterns. It also enables efficient intermolecular formation of all-carbon quaternary stereocenters with high enantioselectivity.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China).
authors.forename: Zhaobin
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China).
authors.forename: Yuk Fai
authors.initials: YF
authors.lastname: Wong
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China). sunjw@ust.hk.
authors.forename: Jianwei
authors.initials: J
authors.lastname: Sun
mesh_terms: D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D045563:Indolequinones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000143:Acids; D045563:Indolequinones; C068040:quinone methide
keywords: asymmetric catalysis; heterocycles; nucleophilic addition; organocatalysis; synthetic methods