Synfacts 2008(7): 0718-0718  
DOI: 10.1055/s-2008-1077849
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Scandium-Catalyzed Enantioselective Addition of α-Cyanoketones to Imines

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
A. Nojiri, N. Kumagai*, M. Shibasaki*
University of Tokyo, Japan
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Publikationsverlauf

Publikationsdatum:
20. Juni 2008 (online)

Significance

The authors report a catalytic asymmetric Mannich-type reaction of α-cyano­ketones and Boc imines with a amide ligand/Sc catalyst, generating consecutive all-carbon quaternary and trisubstituted stereocenters in a highly stereoselective manner. It is noteworthy that precomplexation of ligand and metal is not required and the reaction can be run with ‘one-shot’ addition of all reaction components because the present catalysis proceeds through an ordered association of substrate/ligand and Sc from a conglomerate mixture.