Organocatalytic Asymmetric Atroposelective Construction of Axially Chiral 1,4-Distyrene 2,3-Naphthalene Diols

Organocatalytic Asymmetric Atroposelective Construction of Axially Chiral 1,4-Distyrene 2,3-Naphthalene Diols

An efficient organocatalytic construction of enantioenriched axially chiral 1,4-distyrene 2,3-naphthalene diols through the nucleophilic addition of α-amido sulfone to in situ generated vinylidene o-quinone methide is described. The reaction pathway was investigated by isolating reaction intermediat...

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Veröffentlicht in:Organic letters 2018-12, Vol.20 (23), p.7665-7669
Hauptverfasser: Li, Shan, Xu, Da, Hu, Fangli, Li, Dongmei, Qin, Wenling, Yan, Hailong
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container_issue 23
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container_title Organic letters
container_volume 20
creator Li, Shan
Xu, Da
Hu, Fangli
Li, Dongmei
Qin, Wenling
Yan, Hailong
description An efficient organocatalytic construction of enantioenriched axially chiral 1,4-distyrene 2,3-naphthalene diols through the nucleophilic addition of α-amido sulfone to in situ generated vinylidene o-quinone methide is described. The reaction pathway was investigated by isolating reaction intermediates and performing a kinetic resolution process. Axially chiral 1,4-distyrene 2,3-naphthalene diol was used as the chiral ligand for the enantioselective addition of diethylzinc to naphthalene formaldehyde. The preliminary results revealed that these adducts could be potentially used as ligands in asymmetric synthesis.
doi_str_mv 10.1021/acs.orglett.8b03398
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title Organocatalytic Asymmetric Atroposelective Construction of Axially Chiral 1,4-Distyrene 2,3-Naphthalene Diols
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