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Asymmetric catalytic allylation of halo‐substituted ketones and ketoesters was accomplished to yield a number of homoallylic tertiary alcohols in excellent reactivity and enantioselectivity. In the presence of chiral InIII/N,N′‐dioxide catalyst, unusual α‐selective allylation of γ‐substituted potassium allyltrifluoroborates to ketones was demonstrated. The control experiments and DFT calculation reveal that chiral InIII/N,N′‐dioxide catalyst plays dual‐tasking roles: the formation of allylindium species via transmetalation and Lewis acid activation. A possible reaction pathway was provided to understand α‐selectivity over γ‐selectivity.
Chinese Journal of Chemistry – Wiley
Published: Aug 1, 2022
Keywords: Allylation; Potassium allyltrifluoroborate; Ketones; Indium; Regioselectivity and enantioselectivity
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