Atroposelective Synthesis of Axially Chiral All-Benzenoid Biaryls by the Gold-Catalyzed Intramolecular Hydroarylation of Alkynones

The cationic gold(I)/(R)‐xyl‐binap complex was shown to catalyze the atroposelective intramolecular hydroarylation of alkynones to produce enantioenriched axially chiral all‐benzenoid biaryls, 4‐aryl‐2‐naphthol derivatives, with up to 67 % ee. The reaction of a racemic alkynone in the presence of th...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2016-09, Vol.2016 (26), p.4465-4469
Main Authors: Satoh, Masakazu, Shibata, Yu, Kimura, Yuki, Tanaka, Ken
Format: Article
Language:English
Subjects:
Alkynes
Asymmetric catalysis
Biaryls
Gold
Homogeneous catalysis
Hydroarylation
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:The cationic gold(I)/(R)‐xyl‐binap complex was shown to catalyze the atroposelective intramolecular hydroarylation of alkynones to produce enantioenriched axially chiral all‐benzenoid biaryls, 4‐aryl‐2‐naphthol derivatives, with up to 67 % ee. The reaction of a racemic alkynone in the presence of the same gold(I) catalyst also afforded the corresponding axially chiral all‐benzenoid biaryl in excellent yield with 70 % ee. The cationic gold(I)/(R)‐xyl‐binap complex catalyzes the atroposelective intramolecular hydroarylation of alkynones to produce enantioenriched axially chiral all‐benzenoid biaryls, 4‐aryl‐2‐naphthol derivatives, with up to 67 % ee. The reaction of a racemic alkynone in the presence of the same gold(I) catalyst also affords the corresponding axially chiral all‐benzenoid biaryl in excellent yield with 70 % ee.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600834