Asymmetric para-Functionalization of Anilines Via Chiral Phosphoric Acid Catalysis: Access to CF3-Substituted
Chandrakanta Parida1, Jarosław M Granda1
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Abstract:
We report a chiral phosphoric acid-mediated para-selective functionalization of diphenylamines with propargylic 3-methyleneindoles, enabling the construction of acyclic quaternary stereocenters bearing a trifluoromethyl substituent under mild conditions. This protocol delivers indole-aniline frameworks in good yields and excellent enantioselectivities (up to 99% ee) across 26 examples with a broad tolerance to indole, alkyne, and aniline substitution. Late-stage modification of estrone and l-menthol derivatives and diversification to urea and triazole scaffolds underscore utility, expanding asymmetric para-functionalization of anilines.
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