112683-00-8Relevant academic research and scientific papers
N-Dienyl Lactams: Preparation and Selectivity in the Diels-Alder Reaction
Zezza, Charles A.,Smith, Michael B.
, p. 1161 - 1167 (2007/10/02)
We have shown that N-dienyl lactams are prepared in good yield by reaction of a lactam with an α,β-unsaturated aldehyde.The N-dienyl lactam is obtained with good selectivity for the E,E-isomer.The N-dienyl lactams are excellent enophiles and react with electron-deficient olefins to give exclusively the ortho regioisomer with good selectivity for the endo (Z) adduct, similar to results observed for dienyl amides.In addition, the yield of the Diels-Alder adduct can be significantly enhanced by the use of aqueous solvents when compared to traditional aprotic solvents.
