Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 16, Pages 6295-6300Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406496
Keywords
allylation; hydrides; hydrostannation; small-ring systems; tin
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Funding
- Ministry of Education, Science, Sports, and Culture
- Naito Foundation
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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.
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