NMR investigations on boron complexes in the conjugate addition on alpha,beta-unsaturated imides.
[reaction: see text]. The 1,4-addition of O-benzylhydroxylamine to alpha,beta-unsaturated imide 1 in the presence of BF3.Et2O proceeds with the preferential attack of the nucleophile on the Cbeta-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.
Cardillo
G
G
Dipartimento di Chimica G. Ciamician and CSFM-CNR, Università di Bologna, via Selmi 2, 40126 Bologna, Italy. cardillo@ciam.unibo.it
Gentilucci
L
L
Gianotti
M
M
Tolomelli
A
A
D000535:Aluminum / Q000737:chemistry; D001895:Boron / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry; D006898:Hydroxylamines / Q000737:chemistry; D007094:Imides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical
D002614:Chelating Agents; D006898:Hydroxylamines; D007094:Imides; C017064:benzyloxyamine; D000535:Aluminum; D001895:Boron