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Asymmetric Catalytic α‐Selective Allylation of Ketones with Allyltrifluoroborates Using Dual‐Functional Chiral InIII/N,N′‐Dioxide Complex

Asymmetric Catalytic α‐Selective Allylation of Ketones with Allyltrifluoroborates Using... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chinese Journal of Chemistry Wiley

Asymmetric Catalytic α‐Selective Allylation of Ketones with Allyltrifluoroborates Using Dual‐Functional Chiral InIII/N,N′‐Dioxide Complex

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References (16)

Publisher
Wiley
Copyright
© 2022 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH
eISSN
1614-7065
DOI
10.1002/cjoc.202200166
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Chinese Journal of ChemistryWiley

Published: Aug 1, 2022

Keywords: Allylation; Potassium allyltrifluoroborate; Ketones; Indium; Regioselectivity and enantioselectivity

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