| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5285625 | Tetrahedron Letters | 2008 | 5 Pages |
Abstract
A reductive rearrangement of aminocyclopropanes is described for the synthesis of cis- or trans-fused bicyclic 1,2-diaminocyclobutanes. Ionization of a cyclic aminal using BF3·OEt2 induces rearrangement to a cyclobutyl iminium ion, which is subsequently reduced by Et3SiH. Substitution with allyltrimethylsilane allows carbon incorporation, giving a quaternary center. Silyloxy-substituted cyclopropanes rearrange rapidly to cyclobutanones which react with NaBH4 to provide 1,2-aminohydroxycyclobutanes. These aminals were generated by the reduction of a Boc-imide with DIBAL-H or LiBH4.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Joey L. Methot, Theresa A. Dunstan, Dawn M. Mampreian, Bruce Adams, Michael D. Altman,