Montmorillonite Clay Catalyzed Synthesis of Enantiomerically Pure 1,2,3,4-Tetrahydroquinolines [1]

Abstract

Arylamines undergo smooth cyclization with 2-deoxy-d-ribose on the surface of montmorillonite KSF clay under mild conditions to afford the corresponding sugar-derived chiral tetrahydroquinolines in high yields with moderate diastereoselectivity. The assignment of the stereochemistry of the product was achieved by various NMR studies.

Key words

2-deoxy sugars - solid acid - arylamines - tetrahydroquinolines

1

IICT Communication No. 060501.

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IICT Communication No. 060501.

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Molecular mechanics calculations were carried out using Sybyl 6.8 programme on a silicon graphics O₂ workstation.