Catalytic asymmetric synthesis of cyclopropanecarboxylic acids: An application of chiral copper carbenoid reaction.
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54
摘要：
Reaction of alkyl diazoacetate with an olefin, catalyzed by a chiral copper complex, gives an optically active alkyl cyclopropanecarboxylate. This chiral copper carbenoid reaction was successfully applied to the synthesis of industrially valuable cyclopropanecarboxylic acids: ( plus )-trans-chrysanthemic acid, ( plus )-cis-permethrinic acid and ( plus )-2,2-dimethylcyclopropanecarboxylic acid. A series of effective catalysts, chiral Schiff base-copper complexes, was prepared starting with an optically active alpha -amino acid to achieve more than 90% e. e. of the products. The chirality of the products was correlated with that of the catalyst on the basis of metallacyclobutane intermediates.
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DOI：
10.1351/pac198557121839
被引量：
年份：
1985
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