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Asymmetric Organocatalytic Synthesis of 4-Aminoisochromanones via a Direct One-Pot Intramolecular Mannich Reaction

Fabrizio Vetica, Jeanne Fronert, Rakesh Puttreddy, Kari Rissanen, Dieter Enders*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Email: endersrwth-aachen.de

F. Vetica, J. Fronert, R. Puttreddy, K. Rissanen, D. Enders, Synthesis, 2016, 48, 4451-4458.

DOI: 10.1055/s-0035-1562522 (free Supporting Information)


Abstract

A highly stereoselective one-pot intramolecular Mannich reaction using 2-oxopropyl-2-formylbenzoates and anilines as substrates, catalyzed by a secondary amine, provides 4-aminoisochromanones bearing two adjacent stereocentres in good yields with excellent cis-stereoselectivities and ee values.

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Key Words

organocatalysis, one-pot reaction, asymmetric synthesis, isochromanones, Mannich reaction


ID: J66-Y2016