Asymmetric Pictet-Spengler Reactions: Synthesis of 1,2,3,4-Tetrahydroisoquinoline Carboxylic Acid (Tic) Chimeras

Jan Spengler; Hartmut Schedel; Joachim Sieler; Peter J. L. M. Quaedflieg; Quirinus B. Broxterman; Alexander L. L. Duchateau; Klaus Burger

doi:10.1055/s-2001-16091

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Synthesis 2001(10): 1513-1518
DOI: 10.1055/s-2001-16091

PAPER

Asymmetric Pictet-Spengler Reactions: Synthesis of 1,2,3,4-Tetrahydroisoquinoline Carboxylic Acid (Tic) Chimeras

Jan Spengler^a, Hartmut Schedel^a, Joachim Sieler^b, Peter J. L. M. Quaedflieg^c, Quirinus B. Broxterman^c, Alexander L. L. Duchateau^c, Klaus Burger*^a
^a Department of Organic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: burger@organik.chemie.uni-leipzig.de;
^b Department of Inorganic Chemistry, University of Leipzig, Linnestr. 3, 04103 Leipzig, Germany
^c DSM Research, Life Sciences - Chemistry and Catalysis, P.O. Box 18, 6160 MD Geleen, The Netherlands

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Publication History

Received 13 September 2000
Publication Date:
23 September 2004 (online)

Abstract
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Abstract

A preparatively simple diastereoselective synthesis of the amino acid chimera (1S,3S)-1,2,3,4-tetrahydroisoquinoline-1,3-dicarboxylic acid from hexafluoroacetone-protected phenylalanine and glyoxylic acid hydrate via Pictet-Spengler reaction is described. The potential of the reaction of hexafluoroacetone-protected phenylalanine with other aldehydes was scrutinized.

Key words

amino acids - cyclizations - diastereoselectivity - heterocycles - quinolines

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Crystallographic data for the structural analysis have been deposited at the Cambridge Crystallographic Data Centre, CCDC No. 161191 for 6a. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1233 336033; e-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk).