Rational design of highly effective asymmetric Diels-Alder catalysts bearing 4,4́-sulfonamidomethyl groups

Akira Sakakura, Rei Kondo, Yuki Matsumura, Matsujiro Akakura, Kazuaki Ishihara

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48 Citations (Scopus)

Abstract

(Chemical Equation Presented) The rational design of bis(oxazoline)- copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4́-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

Original languageEnglish
Pages (from-to)17762-17764
Number of pages3
JournalJournal of the American Chemical Society
Volume131
Issue number49
DOIs
Publication statusPublished - Dec 16 2009

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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