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Cu_Zn_Organometallics

its all about organometallic chemistry of zinc and copper metal

Reaction of

Reaction of Organocuprates C-Trapping • Alkylation or hydroxyalkylation (i.e., reaction with RCHO) of enolates derived from conjugate addition of organocuprates affords vicinal dialkylated products. • However, the reaction is confined to highly reactive alkylating agents such as methyl, allyl, propargyl, benzyl, and α-halocarbonyl compounds or aldehydes. • Enolates obtained from conjugate addition of homocuprates or copper-catalyzed Grignard reagents undergo aldol condensation with aldehydes in the presence of ZnCl2 to give stereoisomeric mixtures of aldol products.

Reaction of Organocuprates Stereochemistry of 1,4-addition • Factors controlling the stereochemistry of conjugate additions are not well understood. • Mixtures of isomers are produced, but generally one isomer predominates. Both steric and electronic factors play a role. • Generally, Michael-type additions have late and hence product like — and chairlike—transition states. • example below, for stereoelectronic reasons antiparallel attack by the nucleophilic “CH 3 ”is favored over parallel attack.

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