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Directed ortho-Lithiation of Benzamides
Directed Lithiation of N,N-Diethylbenzamides. Regiospecific Synthesis of Contiguously Tri- and Tetra-Substituted Alkoxybenzenes.
Tetrahedron Lett. 1978;
Snieckus and co-workers reported a regiospecific ortho-lithiation of various N,N-diethylbenzamides using sec-BuLi and TMEDA in THF. The formed lithiated species were trapped with a range of electrophiles and the desired products were obtained in moderate to excellent yield.
The authors demonstrated the utility of this methodology for the synthesis of naturally occurring alkaloids. Thus, a formylated product was converted by successive reduction and cyclization into meconine in 90% yield. Subsequent hydrolysis furnished opianic acid in 50% yield.
18 March 2021 (online)
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