4.4 Article

Concise synthesis of binaphthol-derived chiral dicarboxylic acids

Journal

TETRAHEDRON
Volume 71, Issue 37, Pages 6384-6388

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.05.041

Keywords

Chiral dicarboxylic acid; Reductive CO2 fixation; Directed C-H arylation; Suzuki cross coupling; Organocatalyst

Funding

  1. Astellas Foundation for Research on Metabolic Disorders
  2. grant for Platform for Drug Discovery, Informatics and Structural Life Science from The Ministry of Education, Culture, Sports, Science and Technology, Japan

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3,3'-Disubstituted 1,1'-binaphthy1-2,2'-dicarboxylic acids (1) were synthesized in three or four steps from commercially available BINOL via carbon dioxide fixation with organolithium to incorporate the carboxylic acid moieties, followed by either carboxylate-directed ortho-C-H arylation or Suzuki cross-coupling. This method provides easy access to various types of axiially chiral dicarboxylic acids, which should be useful for studies of chiral Bronsted acid-catalyzed asymmetric reactions. (C) 2015 Elsevier Ltd. All rights reserved.

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