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Issue 10, 2014
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A highly enantioselective acyl-Mannich reaction of isoquinolines with aldehydes promoted by proline derivatives: an approach to 13-alkyl-tetrahydroprotoberberine alkaloids

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Abstract

The highly stereoselective addition of aldehydes to isoquinolines, promoted by the Hayashi–Jørgensen secondary amine catalyst, is described. The procedure has a wide scope, with CbzCl or Boc2O used to activate isoquinoline to nucleophilic addition, allowing for the facile generation of useful synthetic intermediates in high enantiomeric excesses. The products obtained are synthetic intermediates for the synthesis of tetrahydroprotoberberine alkaloids. This methodology has been applied in the first enantioselective synthesis of 13-methyl tetrahydroprotoberberine, as reported herein.

Graphical abstract: A highly enantioselective acyl-Mannich reaction of isoquinolines with aldehydes promoted by proline derivatives: an approach to 13-alkyl-tetrahydroprotoberberine alkaloids

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Article information


Submitted
28 Apr 2014
Accepted
27 Jun 2014
First published
30 Jun 2014

Chem. Sci., 2014,5, 3915-3921
Article type
Edge Article

A highly enantioselective acyl-Mannich reaction of isoquinolines with aldehydes promoted by proline derivatives: an approach to 13-alkyl-tetrahydroprotoberberine alkaloids

L. Mengozzi, A. Gualandi and P. G. Cozzi, Chem. Sci., 2014, 5, 3915
DOI: 10.1039/C4SC01221F

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