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Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines
Paul J. Stevenson,Mark Nieuwenhuyzen,Daire Osborne
Chemical Communications Pub Date : 02/04/2002 00:00:00 , DOI:10.1039/B110242G
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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