Biomaterial Database

Diastereoselective synthesis of P-stereogenic heterocycles via enyne ring-closing metathesis. 2010

James Stephen Harvey, and Guy T Giuffredi, and Véronique Gouverneur

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.

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.

UI	MeSH Term	Description	Entries
D009943	Organophosphorus Compounds	Organic compounds that contain phosphorus as an integral part of the molecule. Included under this heading is broad array of synthetic compounds that are used as PESTICIDES and DRUGS.	Organophosphorus Compound,Organopyrophosphorus Compound,Organopyrophosphorus Compounds,Compound, Organophosphorus,Compound, Organopyrophosphorus,Compounds, Organophosphorus,Compounds, Organopyrophosphorus
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D006571	Heterocyclic Compounds	Cyclic compounds that include atoms other than carbon in their ring structure.	Heterocyclic Compound,Compound, Heterocyclic,Compounds, Heterocyclic
D000480	Alkynes	Hydrocarbons with at least one triple bond in the linear portion, of the general formula Cn-H2n-2.	Acetylenic Compounds,Alkyne,Acetylenes
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular