Stereoselective syntheses of enantiomerically pure 2,5-disubstituted dihydropyrans based on olefin metathesis.
A short synthesis of 2,5-disubstituted dihydropyrans starting from d-mannitol as a chiral building block is described. Our synthetic approach combines ruthenium-catalyzed ring closing olefin metathesis and palladium-catalyzed nucleophilic substitution.
Schmidt
Bernd
B
Universität Potsdam, Institut für Chemie, Organische Chemie II, Karl-Liebknecht-Strasse 24-25, Haus 25, D-14476 Golm, Germany. berschmi@rz.uni-potsdam.de
Nave
Stefan
S
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008353:Mannitol / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D011714:Pyrans; D008353:Mannitol; D010165:Palladium; D012428:Ruthenium