Synthesis

Alkoxycarbonyl-Substituted 3-Trifloxypropene Iminium Salts and Iminium-Substituted Δ2, 3-Butenolides: Synthesis and Reactivity toward Nucleophiles

J Nikolai, G Maas

Index: Nikolai, Joachim; Maas, Gerhard Synthesis, 2003 , # 17 p. 2679 - 2688

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Citation Number: 3

Abstract

Abstract Triflic anhydride reacts regioselectively with the ethoxycarbonyl-substituted enaminones 6a-h to give the novel 3-trifloxypropene iminium salts 7a-d or iminium- substituted Δ 2, 3-butenolides 8a-d and 9a-d in good yields. Hydride reduction of the iminium salts 7a, b affords new 2-dialkylamino-4-trifloxy-but-3-enoates 13a, b, while mild hydrolysis generates 2-oxo-4-trifloxy-butenoates 14a, b. Butenolides 8b, d, and 9c react ...