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Asymmetric Synthesis of Quaternary ‐Perfluorophenyl‐‐Amino‐Indolin‐2‐ones

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Abstract. Reported herein is a design and synthesis of N-tert-butylsulfinyl-(perfluoro)benzaldimine, and study of its reactivity and stereocontrolling properties in the Mannich addition reactions with in situ generated indolinone derived tertiary… Click to show full abstract

Abstract. Reported herein is a design and synthesis of N-tert-butylsulfinyl-(perfluoro)benzaldimine, and study of its reactivity and stereocontrolling properties in the Mannich addition reactions with in situ generated indolinone derived tertiary enolates. The corresponding products, quaternary β- perfluorophenyl-β-amino-indolin-2-ones were obtained with good to excellent yields and diastereoselectivity, underscoring exciting synthetic potential of this newly introduced pentafluorophenyl-containing chiral imine.

Keywords: indolin ones; amino indolin; quaternary perfluorophenyl; perfluorophenyl amino; synthesis

Journal Title: European Journal of Organic Chemistry
Year Published: 2017

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