Diastereoselective synthesis of P-stereogenic heterocycles via enyne ring-closing metathesis.
A range of P-containing ene-diynes suitable for desymmetrization was prepared via a two-step process starting from phosphorus oxychloride. In the presence of the Hoveyda-Grubbs II catalyst, these substrates underwent diastereoselective enyne ring-closing metathesis leading to various synthetically useful P-stereogenic heterocycles featuring an exocyclic alkynyl group. These products are amenable to further functional manipulation.
Harvey
James Stephen
JS
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Giuffredi
Guy T
GT
Gouverneur
Véronique
V
D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D006571:Heterocyclic Compounds; D009943:Organophosphorus Compounds