Download PDF
Synfacts 2011(4): 0397-0397  
DOI: 10.1055/s-0030-1259656
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Cyclopenta- and Cyclo-heptannulation

Contributor(s): Mark Lautens, Jane Panteleev
D. Garayalde, K. Krüger, C. Nevado*
Universität Zürich, Switzerland
Further Information

Publication History

Publication Date:
18 March 2011 (online)

    Permissions and Reprints

Significance

The authors report a gold-promoted reaction cascade leading to five- and seven-membered carbocycles with defined relative ­stereochemistry. Propargyl acetates undergo ­reactions with alkenes to yield cyclopropanation products, which further rearrange through a ring expansion-cyclization reaction. This chemistry is analogous to rhodium-promoted cyclopropanation-cyclo­addition cascades, and is convenient for obviating the use of diazo compounds.