Synfacts 2011(8): 0874-0874  
DOI: 10.1055/s-0030-1260736
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Gold- and Acid-Catalyzed Synthesis of Tetrahydropyrans and Tetrahydrofurans

Contributor(s): Mark Lautens, Stephen G. Newman
B. Bolte, F. Gagosz*
CNRS/Ecole Polytechnique, Palaiseau, France
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Publikationsverlauf

Publikationsdatum:
20. Juli 2011 (online)

Significance

Allenes serve as highly reactive functional groups for the synthesis of complex molecules. The authors present two modes of activation for tethered allenes. Using gold catalysis, fused bicyclic heterocycles are produced. Alternatively Brønsted acid catalysis produces complex tetrahydrofuran spirocycles and tetrahydropyrans with excellent diastereoselectivity.