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Synfacts 2009(11): 1203-1203
DOI: 10.1055/s-0029-1218134
DOI: 10.1055/s-0029-1218134
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Tetrahydroisoquinolines and Tetrahydropyridines from Oxaziridines
C. P. Allen, T. Benkovics, A. K. Turek, T. P. Yoon*
University of Wisconsin-Madison, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Oktober 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200911/lookinside/thumbnails/10.1055-s-0029-1218134-1.jpg)
Significance
Reported here is the synthesis of tetrahydroisoquinolines 2 from N-sulfonyloxaziridines 1 via Cu-catalyzed C-H activation followed by reductive amination. The reaction is tolerant of both EDG and EWG on both aromatic fragments (R¹ and R²). The methodology was extended to include substrates 3 and 6 bearing aliphatic linkers which, upon treatment with acid, generate enamides 5 and piperidones 8, respectively. A mechanism involving coordination of the copper catalyst to the oxaziridine followed by homolytic N-O bond cleavage and cyclization to form a hemiaminal intermediate is proposed.