Functionally active phosphate tethers: Monocyclic phosphate desymmetrization and synthetic utilization

ORGN 687

James P. McParland,, Alan Whitehead,, and Paul R. Hanson, 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

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