Synfacts 2006(8): 0836-0836  
DOI: 10.1055/s-2006-942001
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Addition/Alkylation of Pseudoephedrine Amides

Contributor(s): Paul Knochel, Andrei Gavryushin
E. Reyes, J. L. Vicario, L. Carrillo, D. Badía*, A. Iza, U. Uria
Universidad del País Vasko-Euskal Herriko Unibertsitatea, Bilbao, Spain
Further Information

Publication History

Publication Date:
21 July 2006 (online)

Significance

This work represents an elegant example of asymmetric tandem C-C bond formation reactions. It uses inexpensive pseudoephedrine, available in both enantiomeric forms as a chiral auxiliary. The diastereoselectivity is excellent (above 90%) in most described examples. The reaction proceeds well for β-alkylacrylic derivatives, and both alkyl- and phenyllithium may serve as nucleophiles. The products can be readily transformed into acids by hydrolysis or into the corresponding alcohols by the reduction with lithium aminoboranes.