Asymmetric synthesis of all-carbon quaternary spirocycles via a catalytic enantioselective allylic alkylation strategy |
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| Authors: | Samantha E. Shockley J. Caleb Hethcox Brian M. Stoltz |
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| Affiliation: | The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Blvd, MC 101-20, Pasadena, CA 91125, United States |
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| Abstract: | Rapid access to enantioenriched spirocycles possessing a 1,4-dicarbonyl moiety spanning an all-carbon quaternary stereogenic spirocenter was achieved using a masked bromomethyl vinyl ketone reagent. The developed protocol entails an enantioselective palladium-catalyzed allylic alkylation reaction followed by a one-pot unmasking/RCM sequence that provides access to the spirocyclic compounds in good yields and selectivities. |
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| Keywords: | Allylic alkylation Spirocycle Asymmetric catalysis Palladium catalysis Masked bromomethyl vinyl ketone |
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