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- Title
Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Brønsted Acid Catalysis.
- Authors
Shen, Dan; Chen, Qiliang; Yan, Peipei; Zeng, Xiaofei; Zhong, Guofu
- Abstract
The combination of a transition-metal catalyst and organocatalyst was designed to achieve a highly enantioselective system for the allylic dearomatization reaction of naphthols with racemic secondary allylic alcohols. The desired β-naphthalenones, bearing an all-carbon quaternary center, were obtained in good yields with high chemo- and enantioselectivities. The cooperative catalytic system, involving a chiral iridium complex and phosphoric acid, provided measurable improvements in yields, and chemo- and enantioselectivities relative to single-catalyst systems. Control experiments indicated that the chiral iridium complex functions as a key species in the control of the absolute configuration, thus enabling the formation of both β-naphthalenone enantiomers by simply employing opposite enantiomeric ligands.
- Subjects
ENANTIOSELECTIVE catalysis; NAPHTHOL derivatives; ALLYL alcohol; IRIDIUM catalysts; ACID catalysts; PHENOLS
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 12, p3242
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201609693