Iridium and rhodium complex-catalyzed cycloadditions

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Abstract

Transition metal-catalyzed cycloaddition is an atom-economical and powerful synthetic tool for the construction of cyclic carbon skeletons. Various types of cycloadditions, including [2 + 2 + 1], [2 + 2 + 2], [4 + 2] cycloaddition, etc., have been reported. Their asymmetric versions using chiral transition metal catalysts have also been reported to give enantiomerically-enriched multi-cyclic compounds. First, an iridium-catalyzed enantioselective Pauson-Khand-type reaction is summarized. Pauson-Khand(-type) reaction is a [2 + 2 + 1] cycloaddition of an alkyne, alkene and carbon monoxide, and gives synthetically useful cyclopentenones. Rhodium- and iridium-catalyzed Pauson-Khand-type reactions using an aldehyde as a CO source were also mentioned. Second, two types of enantioselective [2 + 2 + 2] cycloadditions are described: One is an iridium-catalyzed [2 + 2 + 2] cycloaddition of diynes and monoalkynes for the synthesis of chiral teraryls with two axial chiralities. Another is a rhodium-catalyzed [2 + 2 + 2] cycloaddition of enynes and monoalkynes for the synthesis of bicyclic cyclohexa-1, 3-dienes with a chiral quaternary carbon center. Third, a rhodium-catalyzed enantioselective [2 + 2] cycloaddition of alkynes and alkenes for the synthesis of chiral cyclobutenes is mentioned.

Original languageEnglish
Pages (from-to)913-922
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume64
Issue number9
DOIs
Publication statusPublished - 2006 Sep

Keywords

  • Catalysis
  • Chirality
  • Cycloaddition
  • Diynes
  • Enynes
  • Iridium
  • Rhodium

ASJC Scopus subject areas

  • Organic Chemistry

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