What is it about?
Grignard reagents are highly reactive nucleophiles and are usually incompatible with electrophilic functional groups such as carbonates. In this work, we generated a functionalized magnesium alkylidene carbenoid bearing a carbonate group, which undergoes selective intramolecular cyclization to afford α-halobutenolides in only three steps from readily available starting materials.
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Why is it important?
This study demonstrates that a functionalized organomagnesium reagent containing an electrophilic carbonate group can be generated by chemoselective sulfoxide/magnesium exchange and used before undesired intermolecular reactions occur. This expands the synthetic utility of magnesium alkylidene carbenoids and provides an efficient route to valuable α-halobutenolides.
Perspectives
The successful use of a functionalized magnesium alkylidene carbenoid suggests that other organomagnesium reagents bearing compatible electrophilic functional groups could be designed for selective intramolecular bond-forming reactions, broadening the scope of organometallic chemistry.
Associate Professor Tsutomu Kimura
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This page is a summary of: Synthesis of α-Halobutenolides Using the Nucleophilicity of Magnesium Alkylidene Carbenoids, Heterocycles, January 2015, Japan Institute of Heterocyclic Chemistry,
DOI: 10.3987/com-14-s(k)60.
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