177544-93-3Relevant academic research and scientific papers
Lithiated (E)-N-isopropyl-5-tosyl-4-pentenamide: Synthetic applications as new δ-acyldienyl anion equivalent
Caturla, Francisco,Najera, Carmen
, p. 11255 - 11270 (2007/10/03)
The vinyl sulfone (E)-N-isopropyl-5-tosyl-4-pentenamide (14), prepared from 4-pentenoic acid by stereoselective iodosulfonylation-dehydroiodination and further amidation, reacts with two equiv of n-butyllithium at -78°C to give presumably a dilithiated lactam 25. After reaction with aldehydes and propylene oxide or alkyl halides (2E,4E)-6-hydroxy and 7-hydroxy-2,4- hexadienamides 15 and 21 or alkylated dienamides 18 and 20 are stereoselectively obtained, respectively. In the case of carboxylic acid chlorides or cyclohexyl isocyanate, dilithiated lactam 25 undergoes acylation to afford the corresponding lactam derivatives 22. The 6-hydroxy-2,4- dienamide 15f has been transformed into the 6-oxo-2,4-dienamide 41 by oxidation or into the (2E,4E,6E)-trienamide 42 by bromination reactions.
(E)-N-Isopropyl-5-tosyl-4-pentenamide: A vinyl sulfone as precursor of a new δ-acyldienyl anion equivalent
Caturla, Francisco,Najera, Carmen
, p. 2833 - 2836 (2007/10/03)
(E)-N-Isopropyl-5-tosyl-4-pentenamide (7b), prepared from 4-pentenoic acid by stereoselective iodosulfonylation-dehydroiodination and further amidation with oxalyl chloride and isopropylamine, reacts with two equiv of n-butyllithium at -78°C and then with aldehydes affording stereoselectively (2E,4E)-6-hydroxy-2,4-hexadienamides 9. In the case of carboxylic acid chlorides or cyclohexyl isocyanate, dilithiated lactam 8c undergoes acylation to afford the corresponding lactam derivatives 10.
