Enantioselective transformations catalyzed by chiral Brønsted acids

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3 Citations (Scopus)

Abstract

An inventive approach to the development of chiral Brønsted acid catalysts which possess strong acid functionalities has been accomplished. Because of their unique structural and chemical features, phosphoric acids have become the focus of our attention as potential chiral Brønsted acid catalysts, among the various organic Brønsted acids surveyed. An acidic functionality is available even with the introduction of a ring system which effectively restricts the conformational flexibility of the chiral backbone. In addition, substituents can be introduced to the ring system to provide an efficient chiral environment for enantioselective transformations. Furthermore the phosphoryl oxygen would function as a Bronsted basic site and hence it is anticipated that it would convey acid /base dual function even to monofunctional phosphoric acid catalysts. It can be considered that an eficient substrate recognition site would be constructed around the activation site due to the steric and electronic inluence of the substituents introduced at the ring system as well as the acid/base dual function. In this context, we developed 1,1'-bi-2-naphthol (BINOL)-derived monophos-phoric acids as chiral Bronsted acid catalysts. The chiral phosphoric acids thus developed functioned as eficient enantioselective catalysts for a variety of carbon-carbon bond forming reactions via activation of a series of functionalities, affording products in an enantioselective manner. In this account article, we review our recent achievements in developing enantioselective reactions using the chiral phosphoric acid catalysts.

Original languageEnglish
Pages (from-to)480-490
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume71
Issue number5
DOIs
Publication statusPublished - 2013 Jul 24

Keywords

  • Asymmetric catalysis
  • Carbonyl ylide
  • Chiral Bronsted acid
  • Cycloaddition
  • Enantioselectivity
  • Hydrogen bond
  • Imines
  • Mannich reaction
  • Organocatalyst
  • Phosphoric acid

ASJC Scopus subject areas

  • Organic Chemistry

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