A reductive rearrangement of hydroxy- and aminocyclopropyl imides

ORGN 828

Theresa A. Dunstan, dunstan.t@neu.edu and Joey L. Methot, joey_methot@merck.com. Department of Drug Design & Optimization, Merck Research Laboratories, 33 Avenue Louis Pasteur, Boston, MA 02115
A novel aminocyclopropane and hydroxycyclopropane rearrangement is described for the synthesis of 1,2-diamino- and 1,2-aminohydroxycyclobutanes, respectively. Ionization of an aminal with BF3•OEt2/Et3SiH induces ring strain release-driven rearrangement to a cyclobutyl iminium or oxonium ion, which is finally reduced to yield 1,2-diamino- and 1,2-aminohydroxycyclobutanes. These aminals were generated by reduction of a Boc-imide with DIBAL-H. The scope of this transformation will be presented.

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007