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Stereoselective Amidoalkylation Reactions via N,O‐Acetals
Author(s) -
Arenz Thomas,
Frauenrath Herbert,
Raabe Gerhard,
Zorn Martin
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940915
Subject(s) - chemistry , stereoselectivity , isomerization , trimethylsilyl trifluoromethanesulfonate , intermolecular force , trifluoromethanesulfonate , trimethylsilyl , medicinal chemistry , nitrogen , organic chemistry , computational chemistry , stereochemistry , catalysis , molecule
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 mechanism of the reaction is discussed. Crossover experiments indicate an intermolecular course of the rearrangement.