The Michael reaction of silyl enol ethers or ketene silyl acetals with conjugated nitro olefins activated by Lewis acids: new synthesis of 1, 4-diketones and. gamma.-oxo …

…, T Yanami, T Kumazawa, A Yoshikoshi

Index: Miyashita; Yanami; Kumazawa; Yoshikoshi Journal of the American Chemical Society, 1984 , vol. 106, # 7 p. 2149 - 2156

Full Text: HTML

Citation Number: 75

Abstract

Abstract: New one-pot procedures for the synthesis of 1, 4-diketones and y-keto esters utilizing conjugated nitro olefins are described. Reaction of silyl enol ethers with aliphatic nitro olefins in the presence of a Lewis acid affords 1, 4-diketones in good yields, while similar reaction of ketene silyl acetals, derived from various esters, with nitro olefins produces a variety of y-keto esters, after hydrolytic treatment. Regiospecific addition of ...