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

作者：Hahn Robert; Jafari Ehsan; Raabe Gerhard; Enders Dieter^*

来源：Synthesis (Germany), 2015, 47(4): 472-480.

DOI：10.1055/s-0034-1379398

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

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.

• 出版日期2015-2