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

James Stephen Harvey; Guy T Giuffredi; Véronique Gouverneur

doi:10.1021/ol100098c

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

Org Lett. 2010 Mar 19;12(6):1236-9. doi: 10.1021/ol100098c.

Authors

James Stephen Harvey¹, Guy T Giuffredi, Véronique Gouverneur

Affiliation

¹ Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.

PMID: 20184294
DOI: 10.1021/ol100098c

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Cyclization
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry
Molecular Structure
Organophosphorus Compounds / chemistry*
Stereoisomerism

Substances

Alkynes
Heterocyclic Compounds
Organophosphorus Compounds