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1. Asymmetric Synthesis of All-Carbon Quaternary Spirocycles via a Catalytic Enantioselective Allylic Alkylation Strategy

Author

Samantha E. Shockley, J. Caleb Hethcox, and Brian M. Stoltz

Subjects
chemistry.chemical_classification, Ketone, 010405 organic chemistry, Chemistry, Organic Chemistry, Enantioselective synthesis, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Biochemistry, Article, 0104 chemical sciences, Stereocenter, Catalysis, Tsuji–Trost reaction, Reagent, Drug Discovery, Organic chemistry, Moiety, Carbon
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.

Published
2017

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