Construction of Aryliridium−Salen Complexes: Enantio- and Cis-Selective Cyclopropanation of Conjugated and Nonconjugated Olefins

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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.

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