Synfacts 2009(7): 0767-0767  
DOI: 10.1055/s-0029-1217278
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Mannich Reactions Catalyzed by a Dinuclear Nickel Complex

Contributor(s): Mark Lautens, Praew Thansandote
Y. Xu, G. Lu, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
Further Information

Publication History

Publication Date:
22 June 2009 (online)


The authors report an anti-selective asymmetric Mannich reaction catalyzed by a dinuclear zinc Schiff base complex. N-Nosyl imines ­react with α-ketoanilides to give the Mannich products in excellent yields and diastereoselectivities. The products can be subjected to a stereo­selective reduction to afford anti-anti α-hydroxy β-alkyl γ-amino acids, which can then undergo a ­Mitsunobu reaction to form chiral azetidine-2-amides.