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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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.
KeywordsMethyl Zinc Amide Dimethyl Piperidine
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