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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.

SUBMITTER: Hahn R 

PROVIDER: S-EPMC4693956 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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

Hahn Robert R   Jafari Ehsan E   Raabe Gerhard G   Enders Dieter D  

Synthesis 20150201 4

The asymmetric organocatalytic one-pot synthesis of <i>trans</i>-3,4-disubstituted 3,4-dihydroisoquinolin-1(2<i>H</i>)-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 rea  ...[more]

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