Asymmetric Dearomatization of β-Naphthols through an Amination Reaction Catalyzed by a Chiral Phosphoric Acid

A highly efficient catalytic asymmetric dearomatization of naphthols by means of an electrophilic amination reaction catalyzed by chiral phosphoric acid is presented. This protocol provides a facile access to functionalized β‐naphthalenone compounds with a chiral quaternary carbon center in excellen...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-01, Vol.54 (2), p.647-650
Main Authors: Wang, Shou-Guo, Yin, Qin, Zhuo, Chun-Xiang, You, Shu-Li
Format: Article
Language:English
Subjects:
amination reaction
asymmetric catalysis
Asymmetry
Carbon
Catalysis
Catalysts
dearomatization
Naphthol
Natural products
organocatalysis
Phosphoric acid
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A highly efficient catalytic asymmetric dearomatization of naphthols by means of an electrophilic amination reaction catalyzed by chiral phosphoric acid is presented. This protocol provides a facile access to functionalized β‐naphthalenone compounds with a chiral quaternary carbon center in excellent yields and enantioselectivity (up to 99 % yield, up to 96 % ee). Useful skeletons: An electrophilic amination reaction catalyzed by chiral phosphoric acid is the basis for a highly efficient asymmetric dearomatization of naphthols. This protocol provides functionalized β‐naphthalenone compounds with a chiral quaternary carbon center in excellent yields and enantioselectivity. These motifs are found in various biologically active natural products and therapeutic reagents.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201409756