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- W2894840723 abstract "The selective chloromethylenation of functionalized esters using chloroacetic acid (CA) and LiHMDS (HMDS=hexamethyldisilazide) in a continuous-flow setup is reported. This Claisen homologation is for the first time extended to bis-chloromethylenation using dichloroacetic acid (DCA), thus giving access to under-explored α,α'-bis-chloroketones. The use of flow conditions enables efficient generation and reaction of the unstable chloroacetate dianion intermediates, leading to unprecedented mild and scalable reaction conditions at an economical reagent stoichiometry (-10 °C, <1 min, 1.0-2.4 equiv dianion). The clean reaction profiles allow subsequent use of the unpurified crude products, which is demonstrated in the synthesis of various heterocycles of broad interest. Furthermore, we report a novel, catalyst-free substitution of the obtained monochloro ketone products with (hetero)aryl zinc enolates to give valuable 1,4-diketones." @default.
- W2894840723 created "2018-10-12" @default.
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- W2894840723 date "2018-11-27" @default.
- W2894840723 modified "2023-09-24" @default.
- W2894840723 title "Mild Homologation of Esters through Continuous Flow Chloroacetate Claisen Reactions" @default.
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- W2894840723 doi "https://doi.org/10.1002/anie.201810158" @default.
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