A Copper(I)‐Catalyzed Enantioselective γ‐Boryl Substitution of Trifluoromethyl‐Substituted Alkenes: Synthesis of Enantioenriched γ,γ‐<i>gem</i>‐Difluoroallylboronates

Ryoto Kojima, Sota Akiyama, Hajime Ito

Angewandte Chemie International Edition · 2018 · 173 citations · 55 references

Abstract

The first catalytic enantioselective γ-boryl substitution of CF<sub>3</sub> -substituted alkenes is reported. A series of CF<sub>3</sub> -substituted alkenes was treated with a diboron reagent in the presence of a copper(I)/Josiphos catalyst to afford the corresponding optically active γ,γ-gem-difluoroallylboronates in high enantioselectivity. The thus obtained products could be readily converted into the corresponding difluoromethylene-containing homoallylic alcohols using highly stereospecific allylation reactions.

References

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