The asymmetric Ullmann coupling reaction of (S)-2,2'-bis(1-bromo-2-naphthoyloxy)-1,1'-binaphthyl revisited. Formation of 24-membered optically pure cyclic dimer as well as 12-membered cyclic monomer.

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概要

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• The copper-promoted Ullmann reaction of the title diester proceeded with high stereoselectivity to give 24-membered optically pure cyclic dimer of (<I>S</I>,<I>S</I>,<I>S</I>,<I>S</I>)-configuration as well as 12-membered monomeric cycle of (<I>S</I>,<I>S</I>)-configuration. The reaction also gave reduced, open-chain dimer enriched in (<I>S</I>,<I>R</I>,<I>S</I>)-diastereomer over (<I>S</I>,<I>S</I>,<I>S</I>)-counterpart (17% d.e.). Stereochemical course to the cyclic dimer was discussed considering the result that the intermolecular Ullmann coupling of chiral alcohol esters of 1-bromo-2-naphthoic acid poorly induced axial chirality in the joining of the two naphthyl units.

• 公益社団法人 日本化学会の論文

著者

• Miyano Sotaro

  Department Of Biochemistry And Engineering Faculty Of Engineering Tohoku University

• Hashimoto Harukichi

  Department of Applied Chemistry, Faculty of Engineering, Tohoko University

• Tobita Masayuki

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

• Handa Shigeru

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

• Miyano Sotaro

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

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