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Synfacts 2010(2): 0183-0183  
DOI: 10.1055/s-0029-1219095
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed SN2′ Reduction of Propargylic Carbonates

Contributor(s): Hisashi Yamamoto, Pingfan Li
C. Deutsch, B. H. Lipshutz, N. Krause*
Technische Universität Dortmund, Germany and University of California, Santa Barbara, USA
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Publikationsdatum:
21. Januar 2010 (online)

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Significance

A copper-catalyzed SN2′ reduction of propargylic carbonates to functionalized allenes has been developed. The combination of the carbonate leaving group and a suitable N-heterocyclic carbene ligand led to high yield and complete transfer of chirality for this reaction.