Gold-Catalyzed Cycloisomerization of Cyclopropyl Alkynyl Acetates: A Versatile Approach to 5-, 6-, and 7-Membered Carbocycles

Nonclassical chirality transfer? Depending on the substitution pattern of propargyl acetates, a gold‐catalyzed homologous Rautenstrauch reaction generates either 5‐ or 6‐membered ring systems (see scheme). The stabilization of cationic intermediates is crucial for this reaction to succeed. The under...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-01, Vol.47 (52), p.10110-10113
Hauptverfasser: Zou, Yue, Garayalde, David, Wang, Quanrui, Nevado, Cristina, Goeke, Andreas
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Sprache:eng
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Zusammenfassung:Nonclassical chirality transfer? Depending on the substitution pattern of propargyl acetates, a gold‐catalyzed homologous Rautenstrauch reaction generates either 5‐ or 6‐membered ring systems (see scheme). The stabilization of cationic intermediates is crucial for this reaction to succeed. The underlying principle for the good chirality transfer observed could be gold‐stabilized nonclassical carbocations having configurational stability.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200804202