Atroposelective Synthesis of Axially Chiral All‐Benzenoid Biaryls by the Gold‐Catalyzed Intramolecular Hydroarylation of Alkynones. Issue 26 (23rd August 2016)

• Record Type: Journal Article
• Authors: Satoh, Masakazu; Shibata, Yu; Kimura, Yuki; Tanaka, Ken
• Is Part Of: European journal of organic chemistry. Issue 26(2016)
• Page Start: 4465
• Page End: 4469
• Publication Date: 2016-08-23
• Subjects: Asymmetric catalysis -- Homogeneous catalysis -- Gold -- Hydroarylation -- Alkynes -- Biaryls; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600834
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 . Abstract : 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 .