Synfacts 2008(7): 0713-0713  
DOI: 10.1055/s-2008-1077845
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Pd/La Complex for anti-Selective Catalytic Asymmetric Nitroaldol Reactions

Contributor(s):Hisashi Yamamoto, Joshua P. Abell
S. Handa, K. Nagawa, Y. Sohtome, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
A Heterobimetallic Pd/La/Schiff Base Complex for anti-Selective Catalytic Asymmetric Nitroaldol Reactions and Applications to Short Syntheses of β-Adrenoceptor Agonists
Angew. Chem. Int. Ed.  2008,  47:  3230-3233  
Further Information

Publication History

Publication Date:
20 June 2008 (online)


Significance

A limited number of reports describe the anti-selective synthesis of chiral β-amino alcohols. This report describes the design of a simple and efficient catalyst with a broad substrate scope and practical applicability. The authors nicely demonstrate the short syntheses of two β-adrenoceptor agonists.

Comment

Typically the methods for the synthesis of anti-selective chiral β-amino alcohols require the activation of nitroalkanes to silyl­­nitronates. The authors avoid this activation using their het­erobimetallic catalysts extensively studied in their laboratory. This report states that palladium and lanthanum efficiently and selectively produce the desired anti-products in moderate to excellent yields.