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Highly stereoselective synthesis of (Z)-3-methoxy-1-methyleneisoindoles via DMAP catalyzed cyclization of methyl 2-alkynylbenzimidates

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Abstract A DMAP (4-dimethylaminopyridine) catalyzed cyclization of methyl 2-alkynylbenzimidates has been developed, which affords 3-methoxy-1-methyleneisoindoles with excellent Z-stereoselectivity under mild and transition-metal-free conditions. The (Z)-3-methoxy-1-methyleneisoindole products can be converted to… Click to show full abstract

Abstract A DMAP (4-dimethylaminopyridine) catalyzed cyclization of methyl 2-alkynylbenzimidates has been developed, which affords 3-methoxy-1-methyleneisoindoles with excellent Z-stereoselectivity under mild and transition-metal-free conditions. The (Z)-3-methoxy-1-methyleneisoindole products can be converted to corresponding 3-amino-1-methyleneisoindoles, 3-methoxy-isoindoles, 3-methyleneisoindolinones and isoindolinones with high efficiency.

Keywords: catalyzed cyclization; methoxy methyleneisoindoles; dmap; methyl alkynylbenzimidates; cyclization methyl

Journal Title: Tetrahedron
Year Published: 2019

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