Conica can: The In(OTf)3‐catalyzed cyclization of nitrogen‐ and oxygen‐tethered acetylenic malonic esters gives five‐ to seven‐membered heterocycles in moderate to excellent yields (see scheme; Tf=trifluoromethanesulfonyl). The asymmetric synthesis of (−)‐salinosporamide A illustrates the synthetic utility of the method.
Die In(OTf)3‐katalysierte Cyclisierung von Malonsäureestern, die über Stickstoff‐ oder Sauerstoffatome mit acetylenischen Dreifachbindungen verbrückt sind, führt in mäßigen bis ausgezeichneten Ausbeuten zu fünf‐ bis siebengliedrigen Heterocyclen (siehe Beispiel; Tf=Trifluormethansulfonyl). Die asymmetrische Synthese von (−)‐Salinosporamid A illustriert das Anwendungspotenzial der Methode.
A. -The title method is applicable to the synthesis of a broad spectrum of heterocyclic rings and can be used as a key step in the preparation of the desired natural product (XV). -(TAKAHASHI, K.; MIDORI, M.; KAWANO, K.; ISHIHARA, J.; HATAKEYAMA*, S.; Angew. Chem., Int. Ed. 47 (2008) 33, 6244-6246; Grad. Sch. Biomed. Sci., Nagasaki Univ., Nagasaki 852, Japan; Eng.) -Lindner 50-103
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