Concave 1,10-phenanthrolines 1a–c have been used as ligands in the copper(I)-catalyzed cyclopropanation of alkenes 2 with ethyl diazoacetate. The complexes proved to be efficient cyclopropanation catalysts and exhibited an enhanced diastereoselectivity, particularly in the reactions of cyclic alkenes 2b–d. The preferred formation of exo-cyclopropanes 3b–d can be explained by the concave shape of these catalysts.
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Hagen et al. (1997) studied this question.
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