Phosphine-catalysed intermolecular cyclopropanation reaction between benzyl bromides and activated alkenes†
a
and
Ying-Chun
Chen
*ab
Abstract
While phosphine-mediated reactions have been extensively explored over the past few decades, the catalytic cyclopropanation reaction via a phosphonium ylide pathway has been significantly underdeveloped, and an intermolecular version still remains to be disclosed. Presented herein is a catalytic cyclopropanation reaction between readily available benzyl bromides and activated alkenes, such as α-cyano chalcones, through in situ formation of phosphonium ylide intermediates. A spectrum of densely functionalized cyclopropane derivatives is efficiently constructed with excellent diastereoselectivity, which can be further converted to five-membered heterocycles after simple transformations. Moreover, moderate enantioselectivity can be obtained by using a commercially available DuPhos catalyst.
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