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Synfacts 2021; 17(04): 0427
DOI: 10.1055/s-0040-1706718
DOI: 10.1055/s-0040-1706718
Metals in Synthesis
Directed ortho-Lithiation of Benzamides
de Silva SO,
Reed JN,
Snieckus V.
*
University of Waterloo, Canada
Directed Lithiation of N,N-Diethylbenzamides. Regiospecific Synthesis of Contiguously Tri- and Tetra-Substituted Alkoxybenzenes.
Tetrahedron Lett. 1978;
51: 5099-5102
DOI: 10.1016/S0040-4039(01)85822-6.
Directed Lithiation of N,N-Diethylbenzamides. Regiospecific Synthesis of Contiguously Tri- and Tetra-Substituted Alkoxybenzenes.
Tetrahedron Lett. 1978;
51: 5099-5102
DOI: 10.1016/S0040-4039(01)85822-6.
Significance
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.
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Comment
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.
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Publication History
Article published online:
18 March 2021
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