Synfacts 2007(5): 0493-0493  
DOI: 10.1055/s-2007-968439
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed SN2′ Reduction of Propargyl Oxiranes

Contributor(s): Mark Lautens, Yann Béthuel
C. Deutsch, B. H. Lipshutz, N. Krause*
Universität Dortmund, Germany and University of California, Santa Barbara, USA
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24. April 2007 (online)


Allenes and in particular α-hydroxy allenes are synthetically useful building blocks as they can easily be functionalized (see book below). Consequently, their synthesis is a field of intense interest (see book below). Among all methods reported, relatively little interest has been focused on the use of H- in SN2′ reactions. The authors report an efficient methodology based on this concept.