An enantioselective route to alpha-methyl carboxylic acids via metal and enzyme catalysis.
Dynamic kinetic resolution of allylic alcohols to allylic acetates followed by copper-catalyzed allylic substitution gave alkenes in high yields and high optical purity. Subsequent oxidative C-C double bond cleavage afforded pharmaceutically important alpha-methyl substituted carboxylic acids in high ee.
Norinder
Jakob
J
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.
Bogár
Krisztián
K
Kanupp
Lisa
L
Bäckvall
Jan-E
JE
D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005656:Fungal Proteins; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D002264:Carboxylic Acids; D005656:Fungal Proteins; D020005:Propanols; C006463:allyl alcohol; D003300:Copper; D012428:Ruthenium; D008049:Lipase; C431349:lipase B, Candida antarctica