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Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted ?-lactones.

ABSTRACT: New DKR type: An N-heterocyclic carbene (NHC)-catalyzed dynamic kinetic resolution of racemic ?-substituted ?-keto esters has been developed. This method relies on the epimerization of an NHC-enol intermediate before subsequent aldol/acylation events. Highly substituted ?-lactones are produced in good yield with good to excellent selectivities (see scheme).

SUBMITTER: Cohen DT 

PROVIDER: S-EPMC3489928 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Cohen Daniel T DT   Eichman Chad C CC   Phillips Eric M EM   Zarefsky Emily R ER   Scheidt Karl A KA  

Angewandte Chemie (International ed. in English) 20120614 29

New DKR type: An N-heterocyclic carbene (NHC)-catalyzed dynamic kinetic resolution of racemic α-substituted β-keto esters has been developed. This method relies on the epimerization of an NHC-enol intermediate before subsequent aldol/acylation events. Highly substituted β-lactones are produced in good yield with good to excellent selectivities (see scheme). ...[more]

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