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

Abstract

A highly stereoselective one-pot intramolecular Mannich reaction using 2-oxopropyl-2-formylbenzoates and anilines as substrates, catalyzed by a secondary amine, has been developed. The procedure leads to a new class of 4-aminoisochromanones bearing two adjacent stereocentres in good yields (up to 85%) with excellent cis-stereoselectivities (dr up to 99:1) and ee values of 92–99%.

Key words

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

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