A concise synthesis of small to medium-size bicyclic phosphonamidates via ring-closing metathesis is presented. Phosphorus heterocycles are targets of interest for the development of novel biologically active compounds due to their key roles in biological systems and widespread applications in pharmaceutical and agricultural research. Phosphonamidates in particular have gain widespread interest in chemical biology as mimics of the transition state during peptide (amide) bond cleavage by enzymatic hydrolysis. The coupling of unsaturated amino alcohols with allylphosphonyl dichloride assembles <i>P</i>-stereogenic monocyclic metathesis precursors. Upon ring-closing metathesis an array of structurally diverse and stereo-rich bicyclic phosphonamidates are generated.

Concise synthesis of structurally diverse, <i>P</i>-stereogenic bicyclic phosphonamidates by ring-closing metathesis

251st National Meeting (2016)

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Concise synthesis of structurally diverse, P-stereogenic bicyclic phosphonamidates by ring-closing metathesis