Issue 22, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Varun Rawat,a   B. Senthil Kumara  and  Arumugam Sudalai*a  

* Corresponding authors

a Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411008, India
E-mail: a.sudalai@ncl.res.in
Fax: +91-02025902676

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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Article information

DOI
https://doi.org/10.1039/C3OB40320C
Article type
Communication
Submitted
13 Feb 2013
Accepted
24 Apr 2013
First published
25 Apr 2013

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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