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Issue 22, 2013
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Proline catalyzed sequential α-aminooxylation or -amination/reductive cyclization of o-nitrohydrocinnamaldehydes: a high yield synthesis of chiral 3-substituted tetrahydroquinolines

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Abstract

A new sequential organocatalytic method for the synthesis of chiral 3-substituted (X = OH, NH2) tetrahydroquinoline derivatives (THQs) [ee up to 99%, yield up to 87%] based on α-aminooxylation or -amination followed by reductive cyclization of o-nitrohydrocinnamaldehydes has been described. This methodology has been efficiently demonstrated in the synthesis of two important bioactive molecules namely (−)-sumanirole (96% ee) and 1-[(S)-3-(dimethylamino)-3,4-dihydro-6,7-dimethoxy-quinolin-1(2H)-yl]propanone (92% ee).

Graphical abstract: Proline catalyzed sequential α-aminooxylation or -amination/reductive cyclization of o-nitrohydrocinnamaldehydes: a high yield synthesis of chiral 3-substituted tetrahydroquinolines

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Publication details

The article was received on 13 Feb 2013, accepted on 24 Apr 2013 and first published on 25 Apr 2013


Article type: Communication
DOI: 10.1039/C3OB40320C
Citation: Org. Biomol. Chem., 2013,11, 3608-3611
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    Proline catalyzed sequential α-aminooxylation or -amination/reductive cyclization of o-nitrohydrocinnamaldehydes: a high yield synthesis of chiral 3-substituted tetrahydroquinolines

    V. Rawat, B. S. Kumar and A. Sudalai, Org. Biomol. Chem., 2013, 11, 3608
    DOI: 10.1039/C3OB40320C

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