Catalytic asymmetric synthesis of chiral allylic esters.
Trichloroacetimidate derivatives of prochiral (Z)-2-alken-1-ols react at room temperature with carboxylic acids to give chiral 3-acyloxy-1-alkenes in high enantiopurity in the presence of di-mu-acetatobis[(eta5-(S)-(pR)-2-(2'-(4'-methylethyl)oxazolinyl)cyclopentadienyl,1-C,3'-N)(eta4-tetraphenylcyclobutadiene)cobalt]dipalladium (COP-OAc) or its enantiomer. This reaction has broad scope, proceeds with predictable high stereoinduction, is accomplished at room temperature using high substrate concentrations and low catalyst loadings, and likely proceeds by a novel mechanism.
Kirsch
Stefan F
SF
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
Overman
Larry E
LE
D000081:Acetamides; D000498:Allyl Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D062845:Chloroacetates; D004952:Esters / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D000498:Allyl Compounds; D062845:Chloroacetates; D004952:Esters; D010165:Palladium; D014238:Trichloroacetic Acid; C009528:trichloroacetamide
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