Journal
ACS CATALYSIS
Volume 8, Issue 6, Pages 5443-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b00906
Keywords
atroposelective; thiophenol; aryl-naphthoquinone; cinchona alkaloid; biaryl atropisomers
Categories
Funding
- NIH/NIGMS [R35GM124637]
- NIH [5R25GMO58906]
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We report a cinchona alkaloid catalyzed addition of thiophenol into rapidly interconverting aryl-naphthoquinones, resulting in stable biaryl atropisomers upon reductive methylation. An array of thiophenols and naphthoquinone substrates were evaluated, and we observed selectivities up to 98.5:1.5 e.r. Control of the quinone redox properties allowed us to study the stereochemical stabilities of each oxidation state of the substrates. The resulting enantioenriched products can also be moved on via an SNAr-like reaction sequence to arrive at stable derivatives with excellent enantioretention.
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