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Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

ABSTRACT: A highly selective NHC-catalyzed synthesis of ?-butyrolactones from the fusion of enals and ?-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.

SUBMITTER: Jang KP 

PROVIDER: S-EPMC3951019 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Jang Ki Po KP   Hutson Gerri E GE   Johnston Ryne C RC   McCusker Elizabeth O EO   Cheong Paul H-Y PH   Scheidt Karl A KA  

Journal of the American Chemical Society 20131217 1

A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C1-symmetric biaryl-saturated imidazolium-derived NHC catalyst. ...[more]

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