Catalytic asymmetric halofunctionalization of olefins is an arguably important transformation to install two functional groups across C−C double bonds in one step. In recent years, extensive study has been focused on developing halofunctionalization of styrene derivatives and other electron-rich olefins. However, compared with electron-rich alkenes which facilitate the formation of key halonium ion intermediates, the enantioselective halofunctionalization of electron deficient alkenes is less explored.<br/>Based on our previous haloamination of α,β-unsaturated ketones and α,β-unsaturated amides, we present here our recent works on haloazidation and haloetherification of α,β-unsaturated ketones. Chiral organic azides and saturated oxygen heterocycles could be established easily by these methodologies. Kinetic studies and some control experiments suggested that the reaction might proceed via a 1,4-addition/halogenation pathway.

Catalytic asymmetric haloazidation and haloetherification of α,β-unsaturated ketones

256th National Meeting (2018)

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