Download PDF
Synfacts 2006(4): 0366-0366  
DOI: 10.1055/s-2006-934338
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Aza-Henry Reactions Assisted by Zn(II) and N-Methylephedrine

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
C. Palomo*, M. Oiarbide, R. Halder, A. Laso, R. López
Universidad del País Vasco, Spain
Further Information

Publication History

Publication Date:
24 March 2006 (online)

    Permissions and Reprints

Significance

The aza-Henry reaction has been widely studied and other asymmetric variants do exist. This protocol is very significant in that the chiral source is the commercially available N-meth­ylephedrine (NME) and the nitrogen-protecting group is the useful Boc group. The authors found that the use of a base is vital for the reaction, but the particular base used did not matter (various tertiary amines gave acceptable results). Aryl groups with electron-withdrawing groups gave slightly lower enantiomeric excesses than those with electron-donating groups.