Reactions of Zinc Enolates Formed from 1-Aryl-2-bromo-2-phenylethanone or 2-Bromoindanone and Zinc,with Dimethyl 2-(1-Arylmethylene)malonates |
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| Authors: | V V Shchepin A E Korzun M I Vakhrin S N Shurov P S Silaichev M A Ezhikova M I Kodess |
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| Institution: | (1) Perm State University, Perm, Russia;(2) Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, Yekaterinburg, Russia |
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| Abstract: | Zinc enolates formed from 1-aryl-2-bromo-2-phenylethanones and zinc react with dimethyl 2-(1-arylmethylene)malonates to afford dimethyl 2-(1,3-diaryl-3-oxo-2-phenylpropyl)malonates. The latter react with cyclohexylamine, piperidine, or morpholine to give the corresponding monosubstituted amides. The zinc enolate derived from 2-bromoindanone and zinc reacts with dimethyl 2-(4-bromobenzylidene)malonate, yielding dimethyl 2-(4-bromophenyl)(1-oxoindan-2-yl)methyl]malonate. The final products largely form as a single diastereomer. |
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