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...

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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
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description 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.
doi_str_mv 10.1002/ejoc.201600834
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subjects Alkynes
Asymmetric catalysis
Biaryls
Gold
Homogeneous catalysis
Hydroarylation
title Atroposelective Synthesis of Axially Chiral All-Benzenoid Biaryls by the Gold-Catalyzed Intramolecular Hydroarylation of Alkynones
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