Ir-Catalyzed Asymmetric Allylic Alkylation of Dialkyl Malonates Enabling the Construction of Enantioenriched All-Carbon Quaternary Centers.

Farbod A Moghadam, Elliot F Hicks, Zachary P Sercel, Alexander Q Cusumano, Michael D Bartberger, Brian M Stoltz

Journal of the American Chemical Society 2022 May 11

filter terms:

An enantioselective iridium-catalyzed allylic alkylation of malonates with trisubstituted allylic electrophiles to form all-carbon quaternary stereocenters is reported. This reaction proceeds at ambient temperature and enables the preparation of a wide range of enantioenriched products in up to 93% yield and 97% ee. The quaternary products can be readily converted to several valuable building blocks such as vicinal quaternary products and β-quaternary acids.

Citation

Farbod A Moghadam, Elliot F Hicks, Zachary P Sercel, Alexander Q Cusumano, Michael D Bartberger, Brian M Stoltz. Ir-Catalyzed Asymmetric Allylic Alkylation of Dialkyl Malonates Enabling the Construction of Enantioenriched All-Carbon Quaternary Centers. Journal of the American Chemical Society. 2022 May 11;144(18):7983-7987