Perfluorinated Aryls in the Design of Chiral Brønsted Acid Catalysts: Catalysis of Enantioselective [4 + 2] Cycloadditions and Ene Reactions of Imines with Alkenes by Chiral Mono-Phosphoric Acids with Perfluoroaryls

Norie Momiyama, Hiroshi Okamoto, Jun Kikuchi, Toshinobu Korenaga, Masahiro Terada

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Perfluorinated aryl-incorporating chiral monophosphoric acids were used for highly stereoselective reactions of N-acyl and N-acyloxy aldimines with styrenes. Their electronic and steric profiles were established in comparison with those of phenyl, binaphthyl, and partially fluorinated aryls. The [4 + 2] cycloaddition reactions of N-benzoyl aldimines with alkenes proceeded with excellent diastereo- and enantioselectivities in the presence of the perfluorophenyl-incorporating chiral monophosphoric acid catalysts 1a and 1c. The stereoselective elaboration of polysubstituted cycloadducts to amines is described. The imino-ene reactions of N-Fmoc imines with alkenes have been successfully developed in a three-component manner. This process uses aldehydes, 9-fluorenylmethyl carbamate, and alkenes in the presence of a chiral monophosphoric acid catalyst, 2a, possessing an F10binaphthyl skeleton.

Original languageEnglish
Pages (from-to)1198-1204
Number of pages7
JournalACS Catalysis
Volume6
Issue number2
DOIs
Publication statusPublished - 2016 Feb 5

Keywords

  • asymmetric catalysis
  • chiral Brønsted acid
  • cycloaddition
  • iminoene reaction
  • perfluorinated aryls

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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