Synfacts 2007(3): 0282-0282  
DOI: 10.1055/s-2007-968275
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Heterodinuclear Asymmetric Catalyst for Conjugate Additions

Contributor(s): Mark Lautens, Frédéric Ménard
B. M. Trost*, S. Hisaindee
Stanford University, USA
Further Information

Publication History

Publication Date:
20 February 2007 (online)

Significance

Dinuclear catalysts bearing two different metals are not common in asymmetric organo­metallic chemistry although Shibasaki has shown the value of this strategy. The reported Zn/Mg complex 3 was shown to be efficient in the catalytic Michael addition of α-hydroxy ketones to nitroalkenes to access densely functionalized adducts 5-9. The synthetic versatility of the nitro groups in the products 4 was demonstrated in the rapid synthesis of optically active β-amino acids 11 (via LAH reduction, N-protection and oxi­dative cleavage), and one-step synthesis of pyrrolidines 12 via hydrogenation).