Journal of Organic Chemistry p. 4621 - 4628 (1983)
Update date:2022-08-03
Topics:
Marino, Joseph P.
Linderman, Russell J.
The reactivity of substituted (α-carbethoxyvinyl)cuprate reagents with various electrophiles has been studied systematically.The reaction of this type of cuprate reagent with ketones and epoxides leads to high yields of isomerically pure olefinic esters, while its condensation reaction with aldehydes produced mixtures of isomers.The stereochemistry of the condensation reaction with carbonyl compounds is explained by a steric control mechanism involving an allenoate intermediate.
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