The asymmetric Ullmann coupling reaction of chiral diol diesters of 1-bromo-2-naphthoic acid and 2-halo-3-nitrobenzoic acids: Highly diastereoselective synthesis of atropisomeric 6,6'-dinitrodiphenic acids.

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概要

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• The copper-promoted Ullmann reaction of chiral diol diesters of 1-bromo-2-naphthoic acid induced axial dissymmetry into the newly formed 1,1′-binaphthyl bond: chiral diol, apparent net optical yield for the joining of two naphthyl units, and axial chirality induced are as follows: (<I>S</I>)-1,1′-binaphthyl-2,2′-diol, 71%, <I>S</I>; (1<I>S</I>,2<I>S</I>)-1,2-diphenyl-1,2-ethanediol, 32%, <I>S</I>; (1<I>R</I>,2<I>R</I>)-1,2-bis(ethoxycarbonyl)-1,2-ethanediol, 33%, <I>S</I>; (4<I>S</I>,5<I>S</I>)-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane, 3.7%, <I>R</I>. The reaction of (<I>R</I>)-1,1′-binaphthyl-2,2′-diol esters of 2-halo-3-nitrobenzoic acids gave up to 85% net optical yield for the coupling; the intramolecular cyclization proceeded with virtually complete diastereoselectivity to give cyclic diester of <I>R</I>,<I>R</I>-configuration in a 42% isolated yield. This remarkable stereocontrol is ascribed to the steric requirement of the 12-membered cyclic diester structure containing rigid 1,1′-binaphthyl and 1,1′-biphenyl moiety.

• 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

• Handa Shigeru

  Department Of Electronic Engineering Faculity Of Engineering Tohoku University

• Hashimoto Harukichi

  Department of Applied Chemistry, Faculty of Engineering, Tohoko University

• Shimizu Kunitoshi

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

• Tagami Katsuya

  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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