Organoselenium-Catalyzed Asymmetric Cyclopropanations of (E)-Chalcones

We report a new class of chiral tetrahydroselenophene based on (S)-diphenyl(tetrahydroselenophen-2-yl)methanol, which was prepared from (R)-3-(3-bromopropyl)-2,2-diphenyloxirane and sodium selenide. These chiral tetrahydroselenophene-based compounds were used to catalyze asymmetric cyclopropanation reactions; the selenonium ylide intermediates formed from these selenium-containing catalysts and benzyl bromide efficiently react with (E)-chalcones to give various cyclopropanes (27 examples) with excellent enantioselectivities of <= 99% ee and are the first examples of organoselenium-catalyzed asymmetric cyclopropanations.

Automated summary

A new class of chiral tetrahydroselenophene-based compounds were synthesized and demonstrated to catalyze asymmetric cyclopropanation reactions with high enantioselectivities.