New synthesis of (S)-dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate by configuration transform |
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Authors: | Cheng Sen-Xiang Chang Jun-Biao Qu Ling-Bo Chen Rong-Feng |
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Institution: | Center of Research, Henan Academy of Science, Zhengzhou, Henan 450002, China. |
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Abstract: | (R/S)-4,4'-Dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-(4(S)-methyl-oxazoline-1)-biphenyl has been synthesized from dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate, and then the diastereoisomer mixture was almost fully converted to a single diastereoisomer with S-configuration ((S)-3) through the key configuration transform promoted by CuI, which was confirmed by CD, HPLC and (13)C NMR. The C(2)-symmetric biphenyl, (S)-dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate was prepared easily via the hydrolysis and ester exchange of (S)-3. |
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