Enantioselective β-Protonation by a Cooperative Catalysis Strategy.
An enantioselective N-heterocyclic carbene (NHC)-catalyzed β-protonation through the orchestration of three distinct organocatalysts has been developed. This cooperative catalyst system enhances both yield and selectivity, compared to only the NHC-catalyzed process. This new method allows for the efficient conversion of a large scope of aryl-oxobutenoates to highly enantioenriched succinate derivatives and demonstrates the benefits of combining different activation modes in organocatalysis.
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, Illinois 60208, United States.
Michael H
MH
Wang
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, Illinois 60208, United States.
Daniel T
DT
Cohen
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, Illinois 60208, United States.
C Benjamin
CB
Schwamb
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, Illinois 60208, United States.
Rama K
RK
Mishra
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, Illinois 60208, United States.
Karl A
KA
Scheidt
D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D011522:Protons; D011789:Quantum Theory; D013237:Stereoisomerism
D004952:Esters; D006571:Heterocyclic Compounds; D011522:Protons; C030011:carbene; D000171:Acrolein; D008697:Methane; C012843:cinnamaldehyde