Two unexpected but understandable reactions with lithium diisopropylamide (LDA)
Abstract
On treatment with LDA, the acylated oxazolidinones 3 and 10 gave the N-vinylamides 6, 7 and 11 in low yields. The esters 13, on treatment with an excess of LDA at 0 °C, gave a low yield of the β-aminovinyl ketones 15 in addition to the enolates. Methyl benzoate similarly gave the β-aminovinyl ketone 17. Neither the formation of the N-vinylamides nor of the β-aminovinyl ketones was easily made high yielding.