Rhodium-catalyzed enantioselective vinylogous addition of enol ethers to vinyldiazoacetates.

ABSTRACT: A highly asymmetric vinylogous addition of acyclic silyl enol ethers to siloxyvinyldiazoacetate is described. The reaction features a diastereoselective 1,4-siloxy group migration event. Products are obtained in up to 97% ee. When more sterically crowded silyl enol ethers are employed, an enantioselective formal [3+2] cycloaddition becomes the dominant reaction pathway. Control experiments reveal the (Z)-olefin geometry to be critical for high levels of enantiocontrol.

SUBMITTER: Smith AG 

PROVIDER: S-EPMC3549400 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature