RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
Synfacts 2008(10): 1032-1032
DOI: 10.1055/s-2008-1078163
DOI: 10.1055/s-2008-1078163
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Cu-Catalyzed Domino Synthesis of Indolines
A. Minatti, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. September 2008 (online)
Significance
A general domino Cu-catalyzed amidation-intramolecular nucleophilic substitution process leading to indolines in good to excellent yields under very mild conditions is described. In the purported nucleophilic substitution step, mesylates rather than iodo and chloro derivatives were found to be the best substrates. Three mechanistic pathways proceeding via intermediates A-C were proposed. The formation of enantiopure D and racemic cis-E with complete inversion from the corresponding starting materials strongly suggests pathway C to be the operative mechanism.