Synthesis of Naphthoquinone Compounds with Stable Axial Chirality by Addition/Oxidation of Mercaptans
Axial chirality is one of the intrinsic properties of nature and has important significance in organic and medicinal chemistry.Quinone compounds are widely found in natural products,pharma-ceuticals,and other functional molecules.Therefore,constructing quinone compounds with stable chiral axes is an important project.[1,2'-binaphthalene]-1',4'-dione is a class of compounds contai-ning a C—C chiral axis.However,unlike the common 2,2'-disubstituted 1,1'-binaphthalene,their chiral axes have a low rotational energy barrier,and the configuration is unstable at room temperature.Therefore,constructing[1,2'-binaphthalene]-1',4'-dione with stable configuration through simple and efficient reactions is an attractive topic.In this work,a series of naphthoquinone derivatives with stable chiral axes were constructed by the addition/oxidation reaction of mercaptan with different substituted[1,2'-binaphthalene]-1',4'-diones under the catalysis of triethylamine and Cu(OAc)2.The struc-tures of all compounds were characterized by 1H NMR,13C NMR,and HR-MS.
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