4 research outputs found
Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones
No full textWe 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 S<sub>N</sub>Ar-like reaction sequence to arrive
at stable derivatives with excellent enantioretention
Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones
No full textWe 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 S<sub>N</sub>Ar-like reaction sequence to arrive
at stable derivatives with excellent enantioretention
Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones
No full textWe 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 S<sub>N</sub>Ar-like reaction sequence to arrive
at stable derivatives with excellent enantioretention
Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones
No full textWe 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 S<sub>N</sub>Ar-like reaction sequence to arrive
at stable derivatives with excellent enantioretention
