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

Hidehiro Suematsu, Shigefumi Kanchiku, Tatsuya Uchida, Tsutomu Katsuki

Research output: Contribution to journalArticle

75 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

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Alkenes
Olefins
Iridium
Ether
Escherichia coli
Functional groups
Ethers
Esters
Ligands
Catalysts
disalicylaldehyde ethylenediamine
octanoic acid

All Science Journal Classification (ASJC) codes

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

Cite this

Construction of aryliridium-salen complexes : Enantio- and cis-selective cyclopropanation of conjugated and nonconjugated olefins. / Suematsu, Hidehiro; Kanchiku, Shigefumi; Uchida, Tatsuya; Katsuki, Tsutomu.

In: Journal of the American Chemical Society, Vol. 130, No. 31, 06.08.2008, p. 10327-10337.

Research output: Contribution to journalArticle

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