NMR Investigations on Boron Complexes in the Conjugate Addition on α,β-Unsaturated Imides

NMR Investigations on Boron Complexes in the Conjugate Addition on α,β-Unsaturated Imides

The 1,4-addition of O-benzylhydroxylamine to α,β-unsaturated imide 1 in the presence of BF3·Et2O proceeds with the preferential attack of the nucleophile on the Cβ-re face. To explain this unexpected reactivity 1H, 13C, and 11B NMR investigations have been carried out on the boron−imide complex, whi...

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Veröffentlicht in:Organic letters 2001-04, Vol.3 (8), p.1165-1167
Hauptverfasser: Cardillo, Giuliana, Gentilucci, Luca, Gianotti, Massimo, Tolomelli, Alessandra
Format: Artikel
Sprache:eng
Schlagworte:
Aluminum - chemistry
Boron - chemistry
Chelating Agents - chemistry
Hydroxylamines - chemistry
Imides - chemical synthesis
Magnetic Resonance Spectroscopy
Models, Chemical
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Zusammenfassung:The 1,4-addition of O-benzylhydroxylamine to α,β-unsaturated imide 1 in the presence of BF3·Et2O proceeds with the preferential attack of the nucleophile on the Cβ-re face. To explain this unexpected reactivity 1H, 13C, and 11B NMR investigations have been carried out on the boron−imide complex, which show the presence of an S-cis imide chain conformation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015616n