When a mixture of conformationally isomeric enamines, shown below, is treated with
Chapter 22, Problem 22.114(choose chapter or problem)
When a mixture of conformationally isomeric enamines, shown below, is treated with methyl acrylate, followed by aqueous acid, the expected Stork enamine synthesis product A is isolated in 21% ee (Tetrahedron Lett., 1969, 10, 42334236). Assuming that the two enamine isomers are present in equal concentration, explain why such an enantiomeric mixture of A would result in this case by providing a mechanistic analysis for the Michael reaction possible via each enamine. Based on your analysis, determine whether the R or S enantiomer of A predominates in the product mixture and explain your choice. O O OCH3 N CO2Et 1) EtO2C N O OCH3 + 2) H3O+ (Methyl acrylate) A
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