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Synfacts 2009(5): 0527-0527
DOI: 10.1055/s-0029-1216621
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
B. M. Trost*, S. Malhotra, B. A. Fried
Stanford University, USA
Further Information
Publication History
Publication Date:
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.