167149-05-5Relevant academic research and scientific papers
Stereoselective Amidoalkylation Reactions via N,O-Acetals
Arenz, Thomas,Frauenrath, Herbert,Raabe, Gerhard,Zorn, Martin
, p. 931 - 942 (2007/10/02)
The isomerization of N,O-acetals 1 yields N-acyl-O-vinyl acetals 2 or 2-aminomethyl-1,3-butadienes 10, depending on the nature of the nitrogen substituents.In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) the N,O-acetals 2h-u are converted stereoselectively into β-(N-acylamino)aldehydes 3.The relative configurations of the products 3 have been determined by X-ray analysis and 1H-NMR experiments.The mechanism of the reaction is discussed.Crossover experiments indicate an intermolecular course of the rearrangement. - Key Words: N,O-Acetals / Isomerization / Amidoalkylation, stereoselective / β-(N-Acylamino)aldehydes / 2-Aminomethyl-1,3-butadienes
