Synfacts 2009(5): 0527-0527  
DOI: 10.1055/s-0029-1216621
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Aldol Reaction of Diazoacetate Catalyzed by Magnesium

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
B. M. Trost*, S. Malhotra, B. A. Fried
Stanford University, USA
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Publikationsverlauf

Publikationsdatum:
22. April 2009 (online)

Significance

The authors reported a highly enantioselective and general method toward α-diazo-β-hydroxy esters using catalytic direct aldol reaction of ethyl diazoacetate (EDA). Broad substrate scope, commercial availability of reagents and high concentrations (1 M) at which the reactions are performed makes this method very powerful. Furthermore, the authors demonstrated the utility of the products obtained toward synthesis of carbon and heteroatom substituents with high diastereo- and enantioselectivities.