Ring-size-selective enyne metathesis as a tool for desymmetrization of an enantiopure C2-symmetric building block

Bernd Schmidt; Lucia Staude

doi:10.1021/jo9018649

Ring-size-selective enyne metathesis as a tool for desymmetrization of an enantiopure C2-symmetric building block

J Org Chem. 2009 Dec 4;74(23):9237-40. doi: 10.1021/jo9018649.

Authors

Bernd Schmidt¹, Lucia Staude

Affiliation

¹ Institut fuer Chemie, Organische Synthesechemie, Universitaet Potsdam, Karl-Liebknecht-Strasse 24-25, D-14476 Golm, Germany. [email protected]

PMID: 19905005
DOI: 10.1021/jo9018649

Abstract

The enantiomerically pure C(2)-symmetrical hexa-1,5-diene-3,4-diol is selectively monopropargylated. The products undergo ring-closing enyne metathesis to give exclusively dihydropyrans as single stereoisomers. An unprotected hydroxy group is identified as the factor controlling the ring-size selectivity.