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. 2015 Feb 1;47(4):472-480.
doi: 10.1055/s-0034-1379398.

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

Robert Hahn  1 , Ehsan Jafari  1 , Gerhard Raabe  1 , Dieter Enders  1
Affiliations

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

Robert Hahn et al. Synthesis (Stuttg). .

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.

Keywords: dihydroisoquinolinones; domino reaction; hydrogen bonding; one-pot reaction; organocatalysis.

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Figures

Figure 1
Figure 1
Selected examples of naturally and synthetically derived dihydroisoquinolinones
Figure 2
Figure 2
Determination of the absolute configuration of compound 11a by X-ray crystal structure analysis
Scheme 1
Scheme 1
2-(Nitromethyl)benzaldehydes as bifunctional substrates in asymmetric organocatalytic domino reactions
See this image and copyright information in PMC

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