Asymmetric Synthesis of All-Carbon Quaternary Spirocycles via a Catalytic Enantioselective Allylic Alkylation Strategy
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.
Additional Information© 2017 Elsevier Ltd. Received 27 June 2017, Accepted 3 July 2017, Available online 5 July 2017. The NIH-NIGMS (R01GM080269) and Caltech are thanked for support of our research program. J.C.H. thanks the Camille and Henry Dreyfus postdoctoral program, and S.E.S. thanks the NIH-NIGMS for a predoctoral fellowship (F31GM120804). Dr. Mona Shahgholi and Naseem Torian (Caltech) are thanked for mass spectrometry assistance. Dr. Scott Virgil (Caltech) is thanked for assistance with instrumentation.
Accepted Version - nihms894924.pdf
Supplemental Material - 1-s2.0-S0040403917308559-mmc1.pdf