Synfacts 2011(5): 0512-0512  
DOI: 10.1055/s-0030-1259832
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Asymmetric Allylic Alkylation

Contributor(s): Mark Lautens, Jane Panteleev
J.-B. Langlois, A. Alexakis*
University of Geneva, Switzerland
Further Information

Publication History

Publication Date:
15 April 2011 (online)

Significance

The authors describe mechanistic studies on the kinetic resolution of racemic linear allyl chlorides. Following their work on the alkylation of cyclic substrates (Chem. Commun. 2009, 3868), this work reveals a much more complex stereodivergent resolution yielding products as mixtures of E/Z isomers. In addition to the interesting mechanistic insight of this work, the product mixture could be convergently transformed to afford chiral synthons in high yields.