4.6 Article

Transition-Metal-Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 16, Pages 6295-6300

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406496

Keywords

allylation; hydrides; hydrostannation; small-ring systems; tin

Funding

  1. Ministry of Education, Science, Sports, and Culture
  2. Naito Foundation

Ask authors/readers for more resources

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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.6
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available