Download PDF
Synfacts 2011(9): 0976-0976  
DOI: 10.1055/s-0030-1261007
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Cu/Box-Catalyzed Mukaiyama-Michael Additions towards Chiral Diazoacetoacetates

Contributor(s): Mark Lautens, Hasnain A. Malik
X. Xu, W.-H. Hu, M. P. Doyle*
University of Maryland, College Park, USA and East China Normal University, Shanghai, P. R. of China
Further Information

Publication History

Publication Date:
19 August 2011 (online)

    Permissions and Reprints

Significance

The authors report a copper-catalyzed asymmetric synthesis of γ-functionalized ­diazoacetoacetates via Mukaiyama-Michael addition reactions. Careful reaction optimization efforts led to a reaction that resulted in moderate to good yields with moderate to good enantioselectivities using a chiral Box ligand. The authors demonstrate the synthetic utility of their products by showcasing the synthesis of chiral 1,5-diesters.