Catalytic enantioselective decarboxylative protonation.
We report a highly enantioselective, general catalytic system for the facile synthesis of tertiary stereocenters by protonation adjacent to cyclic ketones. The method relies on catalytic decarboxylative protonation of readily accessible racemic quaternary beta-ketoesters. A range of substituted cycloalkanone compounds can be accessed through this process with high levels of enantioselectivity.
Mohr
Justin T
JT
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Nishimata
Toyoki
T
Behenna
Douglas C
DC
Stoltz
Brian M
BM
D002384:Catalysis; D003653:Decarboxylation; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011522:Protons; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D007659:Ketones; D011522:Protons; D012997:Solvents; D010165:Palladium