Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines.
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.
Stevenson
Paul J
PJ
School of Chemistry, Queen's University of Belfast, Belfast, UK. p.stevenson@qub.ac.uk
Nieuwenhuyzen
Mark
M
Osborne
Daire
D