Construction of aryliridium-salen complexes: Enantio- and cis-selective cyclopropanation of conjugated and nonconjugated olefins

Hidehiro Suematsu, Shigefumi Kanchiku, Tatsuya Uchida, Tsutomu Katsuki

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79 Citations (Scopus)

Abstract

Two stable and optically active iridium-salen complexes were synthesized by introducing a tolyl or phenyl ligand at the apical position, respectively, via the SEAr mechanism, and they were found to be efficient catalysts for cis-selective asymmetric cyclopropanation. The scope of the cyclopropanation was wide, and the reactions of not only conjugated mono-, di-, and trisubstituted olefins but also nonconjugated terminal olefins proceeded with high enantio- and cis-selectivity, even in the presence of a functional group such as an ether or ester. The utility of this cyclopropanation was demonstrated by a short step synthesis of 8-[(1R,2S)-2-hexylcyclopropyl]octanoate, isolated from Escherichia coli B-ATCC 11303, using the reaction as the key step.

Original languageEnglish
Pages (from-to)10327-10337
Number of pages11
JournalJournal of the American Chemical Society
Volume130
Issue number31
DOIs
Publication statusPublished - Aug 6 2008

All Science Journal Classification (ASJC) codes

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

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