Functionally active phosphate tethers: Monocyclic phosphate desymmetrization and synthetic utilization

ORGN 687

James P. McParland, jmcparl@ku.edu, Alan Whitehead, alanwh@ku.edu, and Paul R. Hanson, phanson@ku.edu. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr, Malott Hall, Lawrence, KS 66045-7582
Monocyclic pseudo-C2-symmetric phosphate triesters are rapidly assembled via a phosphate tether-mediated ring-closing metathesis reaction. Symmetry breaking, stereoselective anti-SN2'-allylic cuprate displacements are utilized to yield non-racemic, highly functionalized building blocks. Efforts are currently underway in applying these phosphorous building blocks in total synthesis. The phosphate moiety serves a multi-faceted role as a tether, leaving group, and protecting group.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005