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Issue 5, 2002
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Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines

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Abstract

N-Acetyl-2-azetine undergoes Lewis acid catalysed [4 + 2]-cycloaddition with imines derived from aromatic amines and gave a 1∶1 mixture of exo–endo diastereoisomeric azetidine cycloadducts which reacted further with aromatic amine, to give 2,3,4-trisubsitituted tetrahydroquinolines in good to excellent yield, predominantly as one diastereoisomer.

Graphical abstract: Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines

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Article information


Submitted
13 Nov 2001
Accepted
03 Jan 2001
First published
04 Feb 2002

Chem. Commun., 2002, 444-445
Article type
Communication

Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines

P. J. Stevenson, M. Nieuwenhuyzen and D. Osborne, Chem. Commun., 2002, 444
DOI: 10.1039/B110242G

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