Synfacts 2008(3): 0278-0278  
DOI: 10.1055/s-2008-1042694
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Nd/Na-Catalyzed Anti-Selective Nitroaldol Reaction

Contributor(s): Mark Lautens, Praew Thansandote
T. Nitabaru, N. Kumagai*, M. Shibasaki*
The University of Tokyo, Japan
Further Information

Publication History

Publication Date:
21 February 2008 (online)

Significance

A catalytic asymmetric anti-selective nitroaldol reaction has been developed using a Nd/Na/amide heterobimetallic catalyst. The yields, diastereoselectivities, and enantioselectivities are highest with aromatic aldehydes with an ortho-alkyl substituent. The products are useful anti-1,2-nitro alkanols, which can be rapidly converted into synthetically useful anti-1,2-amino alcohols.