Journal of Organic Chemistry p. 2857 - 2863 (1984)
Update date:2022-08-05
Topics: Michael reaction Ester enolates New Synthesis Conjugated Nitro Olefins Carboxylic Acid Dianions γ-Keto Acids γ-Keto Esters
Miyashita, Masaaki
Yamaguchi, Ryuji
Yoshikoshi, Akira
Base-sensitive conjugated nitro olefins 2 reacted with lithium dianions of carboxylic acids 3 or with lithium enolates of esters 4 at a low temperature of ca. -100 deg C, and subsequent treatment of the Michael adducts with aqueous acid yielded γ-keto acids 5 or esters 5' in a one-pot operation, respectively.Results of both the reactions have been compared.Some applications of the resulting γ-keto esters in organic synthesis have also been demonstrated in lactone synthesis and cyclenone annulation.
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