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Enantioselective ?-Protonation by a Cooperative Catalysis Strategy.

ABSTRACT: An enantioselective N-heterocyclic carbene (NHC)-catalyzed ?-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.

SUBMITTER: Wang MH

PROVIDER: S-EPMC4492478 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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Enantioselective β-Protonation by a Cooperative Catalysis Strategy.

Wang Michael H MH Cohen Daniel T DT Schwamb C Benjamin CB Mishra Rama K RK Scheidt Karl A KA

Journal of the American Chemical Society 20150504 18

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. ...[more]

PMID: 25929160

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