Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence

Abstract

The asymmetric organocatalytic one-pot synthesis of trans-3,4-disubstituted 3,4-dihydroisoquinolin-1(2H)-ones is described. Starting from 2-(nitromethyl)benzaldehydes and various N-protected aldimines, 5 mol% of a quinine-based squaramide organocatalyst was used to synthesize the title compounds as virtually single diastereomers via an aza-Henry–hemiaminalization–oxidation sequence. Moderate to good yields (39–78%) and moderate to very good enantioselectivities (40–95% ee) were reached.

Key words

organocatalysis - domino reaction - one-pot reaction - dihydroisoquinolinones - hydrogen bonding

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