Synfacts 2010(5): 0564-0564  
DOI: 10.1055/s-0029-1219694
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Cycloalkenes by an Asymmetric Allylic Alkylation-RCM Procedure

Contributor(s): Mark Lautens, Stephen G. Newman
F. Giacomina, D. Riat, A. Alexakis*
University of Geneva, Switzerland
Further Information

Publication History

Publication Date:
22 April 2010 (online)

Significance

Copper-catalyzed asymmetric allylic alkylation reactions (AAA) allow the addition of hard nucleophiles (e.g., Grignard reagents) to electrophiles with high enantioselectivity. This method is limited to prochiral substrates and the use of chiral cyclic electrophiles is not possible. The authors present a method to overcome this restriction by using AAA of achiral linear substrates, followed by an RCM to furnish the desired cyclic compounds.