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(NHC)CuH-Catalyzed Entry to Allenes via Propargylic Carbonate SN2'-Reductions

Carl Deutsch, Bruce H. Lipshutz and Norbert Krause*

*Organic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany, Email: norbert.krausetu-dortmund.de

C. Deutsch, B. H. Lipshutz, N. Krause, Org. Lett., 2009, 11, 5010-5012.

DOI: 10.1021/ol901868m (free Supporting Information)


Abstract

A copper hydride-catalyzed SN2′-reduction of propargylic carbonates provides functionalized allenes in good yields. The method takes advantage of the stabilizing effect of NHC ligands on CuH and offers high reactivity, stereoselectivity, and functional group tolerance.


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Key Words

Allenes, Copper Hydride, PMHS


ID: J54-Y2009-3240