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 excell...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2002-03 (5), p.444-445
Hauptverfasser: Stevenson, Paul J, Nieuwenhuyzen, Mark, Osborne, Daire
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/b110242g