Transition-metal-free coupling reaction of vinylcyclopropanes with aldehydes catalyzed by tin hydride

Chemistry : a European Journal
Ryosuke IekiIkuya Shibata

Abstract

Donor-acceptor cyclopropanes are useful building blocks for catalytic cycloaddition reactions with a range of electrophiles to give various cyclic products. In contrast, relatively few methods are available for the synthesis of homoallylic alcohols through coupling of vinylcyclopropanes (VCPs) with aldehydes, even with transition-metal catalysts. Here, we report that the hydrostannation of vinylcyclopropanes (VCPs) was effectively promoted by dibutyliodotin hydride (Bu2 SnIH). The resultant allylic tin compounds reacted easily with aldehydes. Furthermore, the use of Bu2 SnIH was effectively catalytic in the presence of hydrosilane as a hydride source, which established a coupling reaction of VCPs with aldehydes for the synthesis of homoallylic alcohols without the use of transition-metal catalysts. In contrast to conventional catalytic reactions of VCPs, the presented method allowed the use of several VCPs in addition to conventional donor-acceptor cyclopropanes.

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Citations

May 18, 2016·Organic Letters·Tsuyoshi MitaYoshihiro Sato
Feb 25, 2017·Organic & Biomolecular Chemistry·Marta MeazzaRamon Rios
Dec 10, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alexander A FadeevIgor V Trushkov
Jun 28, 2019·The Journal of Organic Chemistry·Palasetty ChanduDevarajulu Sureshkumar

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