Synthesis 2001(10): 1513-1518
DOI: 10.1055/s-2001-16091
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Jan Spenglera, Hartmut Schedela, Joachim Sielerb, Peter J. L. M. Quaedfliegc, Quirinus B. Broxtermanc, Alexander L. L. Duchateauc, 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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Publikationsverlauf

Received 13 September 2000
Publikationsdatum:
23. September 2004 (online)

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.

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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).