4.5 Article

Enantioselective Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Phosphoric Acid Catalysts

Journal

CURRENT ORGANIC CHEMISTRY
Volume 15, Issue 13, Pages 2227-2256

Publisher

BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/138527211796150732

Keywords

Bronsted acid; diels-alder reaction; enantioselectivity; ene reaction; friedel-crafts reaction; hydrogen bond; mannich reaction; organocatalysis

Funding

  1. Ministry of Education, Culture, Sports, and Science and Technology, Japan
  2. Grants-in-Aid for Scientific Research [23655077] Funding Source: KAKEN

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Chiral phosphoric acids derived from axially chiral biaryls and analogous chiral Bronsted acids have emerged as an attractive and widely applicable class of enantioselective organocatalysts for a variety of organic transformations. In this account article, we review our recent achievements and related works in the development of enantioselective carbon-carbon bond forming reactions using these axially chiral phosphoric acids and their analogues as chiral Bronsted acid catalysts. The contents are arranged according to the type of (pro) electrophiles, including imines, hemiaminal ethers, carbonyl compounds, and electron-rich double bonds, followed by specific reaction types. Further application to phosphoric acid/metal complex-combined catalytic systems is also highlighted.

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