Desymmetrization of diols by a tandem oxidation/Wittig olefination reaction.
Diols are desymmetrized by a tandem oxidation/Wittig olefination to give alpha,beta-unsaturated hydroxy esters without the requirement for protecting group strategies; the alpha,beta-unsaturated hydroxy esters are transformed into dienyl diesters using a second oxidation/Wittig olefination sequence using PCC.
Phillips
David J
DJ
Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea, UK SA2 8PP.
Pillinger
Kathryn S
KS
Li
Wei
W
Taylor
Angela E
AE
Graham
Andrew E
AE
D000475:Alkenes / Q000737:chemistry*; D002072:Butylene Glycols / Q000737:chemistry*; D002625:Chemistry, Organic; D004952:Esters / Q000737:chemistry*; D017895:Manganese Compounds / Q000737:chemistry; D055601:Organic Chemistry Phenomena; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D002072:Butylene Glycols; D004952:Esters; D017895:Manganese Compounds; D010087:Oxides; C039681:1,4-butanediol; C016552:manganese dioxide