Transition‐Metal‐Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride |
| |
| Authors: | Ryosuke Ieki Yuria Kani Dr. Shinji Tsunoi Prof. Ikuya Shibata |
| |
| Affiliation: | Research Center for Environmental Preservation, Osaka University, 2‐4 Yamadaoka, Suita, Osaka 565‐0871 (Japan) |
| |
| 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 (Bu2SnIH). The resultant allylic tin compounds reacted easily with aldehydes. Furthermore, the use of Bu2SnIH 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. |
| |
| Keywords: | allylation hydrides hydrostannation small‐ring systems tin |
|
|
