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Enantioselective Synthesis of Axially Chiral N‐Aryl‐3‐methyleneisoindolin‐1‐ones

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Asymmetric condensation of 2-acetylbenzoic acid derivatives with 2-substituted aniline derivatives provided various axially chiral N-aryl-3-methyleneisoindolin-1-ones in moderate to good yields with generally moderate enantioselectivities.


Abstract

3-Methyleneisoindolin-1-one units exist in many natural products and pharmaceutics. Up to now, synthesis of axially chiral 3-methyleneisoindolin-1-ones has been rarely reported. Herein we disclose a chiral phosphoric acid catalyzed enantioselective condensation of 2-acetylbenzoic acid derivatives with 2-substituted aniline derivatives, leading to the construction of a series of novel C−N axially chiral N-aryl-3-methylene-isoindolin-1-ones in moderate to good yields (up to 97%) with generally moderate enantioselectivities (up to 87% ee). In addition, the absolute configuration of one product was determined by an X-ray crystal structural analysis. Furthermore, one product was subjected to oxidative cleavage to generate an axially chiral phthalimide.

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