Synthesis of fluorine containing heterocycles via Prins methodology

ORGN 736

Mark J Penny, m.j.penny@qmul.ac.uk1, Adrian P Dobbs, A.Dobbs@qmul.ac.uk1, Levan Pivnevi, lpivnevi@yahoo.co.uk2, Peter Stephenson2, and Peter Jones, Peter.Jones2@pfizer.com3. (1) Department of Chemistry, Queen Mary University of London, Mile End Road, London, E1 4NS, United Kingdom, (2) Department of Chemistry, The Open University, Walton Hall, Milton Keynes, MK7 6AA, (3) Discovery Chemistry, Pfizer Global R&D, Sandwich, Kent, CT13 9NJ, United Kingdom
Fluorine containing molecules are of great importance to the pharmaceutical industry and many analogues of biologically active or natural molecules with enhanced activities contain fluorine, often as a replacement for the hydroxyl group.

Herein we describe the synthesis of a variety of fluorinated tetrahydropyrans and piperidines via the Prins methodology from commercially available aldehydes and fluorinated building blocks – fluorinated homoallylic alcohols or amines. The presence of the electronegative fluorine atom appears to have only a modest effect on the stability of the intermediate adjacent carbocation.

 

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