Synfacts 2007(5): 0535-0535  
DOI: 10.1055/s-2007-968431
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Al-Catalyzed Asymmetric Mukaiyama-Michael Reaction and Indole Friedel-Crafts Alkylation

Contributor(s): Paul Knochel, Tobias Thaler
N. Takenaka, J. P. Abell, H. Yamamoto*
The University of Chicago, USA
Further Information

Publication History

Publication Date:
24 April 2007 (online)


The use of (TBOx)AlSbF6 as chiral catalyst in the Mukaiyama-Michael reaction and the indole Friedel-Crafts reaction is reported. The reactions proceed with excellent enantioselectivities delivering the desired products in acceptable to excellent yields. Si(OEt)3-protected enol ethers undergo the Mukayiama-Michael reaction at lower temperatures than their TMS-protected analogues. The diastereoselectivities in the reactions of tetrasubstituted enolates can thus be improved.