ISSN:
0170-2041
Schlagwort(e):
N,O-Acetals
;
Isomerization
;
Amidoalkylation, stereoselective
;
β-(N-Acylamino)aldehydes
;
2-Aminomethyl-1,3-butadienes
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
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.
Zusätzliches Material:
2 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.199419940915
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