Synfacts 2007(8): 0837-0837  
DOI: 10.1055/s-2007-968729
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Au-Catalyzed Diastereoselective [3+2] Cycloaddition

Contributor(s): Mark Lautens, Praew Thansandote
X. Huang, L. Zhang*
University of Nevada, Reno, USA
Further Information

Publication History

Publication Date:
24 July 2007 (online)

Significance

A gold-catalyzed diastereoselective [3+2] cycloaddition of an allenyl MOM ether with enals or enones is shown to create synthetically useful cyclopentanone enol ethers with all-carbon quaternary centers. The one-pot, two-step reaction first involves silylation of the enal or enone (which increases selectivity) followed by cycloaddition, eliminating the isolation of the delicate intermediate. The scope is broad for both acyclic and cyclic enals and enones with single diastereo­mers seen.