Ring-size-selective enyne metathesis as a tool for desymmetrization of an enantiopure C2-symmetric building block.
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.
Schmidt
Bernd
B
Institut fuer Chemie, Organische Synthesechemie, Universitaet Potsdam, Karl-Liebknecht-Strasse 24-25, D-14476 Golm, Germany. bernd.schmidt@uni-potsdam.de
Staude
Lucia
L