Metalated unsaturated amides. Regio-and stereoselective. gamma.-alkylation

M Majewski, GB Mpango, MT Thomas…

Index: Majewski, M.; Mpango, G. B.; Thomas, M. T.; Wu, A.; Snieckus, V. Journal of Organic Chemistry, 1981 , vol. 46, # 10 p. 2029 - 2045

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Citation Number: 57

Abstract

The reactions of lithiated and dilithiated unsaturated amides 4, 5, 12, 15, 18, 34, and 36 with a variety of electrophiles have been shown to produce deconjugated, a-alkylated products 6, 7, 13, 16, 19, 35, and 37, respectively, in good to excellent yields (Tables I, 11, IV, and VI). Whereas lithiated 4 and dilithiated 5 do not undergo y-alkylation, the corresponding species of 12 and 15, when converted to their cuprates by using cuprous iodide, afford y products ...