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Synthesis 2001; 2001(4): 0612-0620
DOI: 10.1055/s-2001-12345
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Ring-Closing Metathesis Strategies to Amino Acid-Derived P-Heterocycles

Kevin T. Sprott* , Matthew D. McReynolds, Paul R. Hanson
  • *Department of Chemistry, University of Kansas, Lawrence, KS 66045-2506, USA; Fax + 1(785)8 64 30 94; E-mail: phanson@ukans.edu
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Publication Date:
31 December 2001 (online)

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Utilization of the ring-closing metathesis (RCM) reaction in the synthesis of a number of amino acid-derived 5- and 7-membered cyclic phosphorus-containing compounds is described. Coupling of achiral and non-racemic allylic amines with P(V) and P(III) chlorides generates acyclic phosphorus-containing metathesis precursors. These templates undergo RCM in the presence of the Grubbs benzylidene catalyst to afford an array of amino acid-based P-heterocycles.

ring-closing metathesis - ruthenium - anhydride - peptidomimetic - phosphorus - heterocycles

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