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Organocatalytic Asymmetric Atroposelective Construction of Axially Chiral 1,4-Distyrene 2,3-Naphthalene Diols. 2018
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences , Chongqing University , Chongqing 401331 , P. R. China.
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.
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