Asymmetric Synthesis of 3-Substituted Dihydro-2H-isoquinolin-1-ones, Dihydro- and Tetrahydroisoquinolines via 1,2-Addition/Ring Closure

Dieter Enders; Volker Braig; Marine Boudou; Gerhard Raabe

doi:10.1055/s-2004-834861

PAPER

Asymmetric Synthesis of 3-Substituted Dihydro-2H-isoquinolin-1-ones, Dihydro- and Tetrahydroisoquinolines via 1,2-Addition/Ring Closure

Dieter Enders*, Volker Braig, Marine Boudou, Gerhard Raabe
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52 074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: Enders@rwth-aachen.de;

Abstract

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Abstract

The asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro- and tetrahydroisoquinolines is described. The key operation is a tandem 1,2-addition/ring closure sequence employing lithiated ortho-toluamides and aldehyde SAMP- or RAMP-hydrazones as substrates, followed by N-N bond cleavage to remove the auxiliary. Moderate to good yields and high enantiomeric excesses (ee = 85-99%) are reached.

Key words

asymmetric synthesis - nucleophilic addition - cyclisation - hydrazones - heterocycles

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References

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