Stereoselective Amidoalkylation Reactions via N, O??Acetals

T Arenz, H Frauenrath, G Raabe…

Index: Arenz, Thomas; Frauenrath, Herbert; Raabe, Gerhard; Zorn, Martin Liebigs Annalen der Chemie, 1994 , # 9 p. 931 - 942

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Citation Number: 9

Abstract

Abstract 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 1 H-NMR experiments. The ...