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

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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23

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: [phone]; e-mail: [e-mail] or http://www.ccdc.cam.ac.uk).