Wondering why your blog was not aggregated by Chemical blogspace yet... http://cb.openmolecules.net/ - Egon Willighagen

The cyclization might happen if the alcohol could be protonated with an acid catalyst. You have the huge benefit of forming a 5 membered ring. - Jean-Claude Bradley

Egon - just set the blog up. Finally. JC - I think even with the protonation, a direct displacement would be difficult. With that double bond in there, and the flattish amide, I don't think the nitrogen can reach round to do a direct displacement. - Matthew Todd

Mat - sure it has a lot going against it but might still be worth trying - Jean-Claude Bradley

I'd be tempted to deprotonate (you're stabilized by both alcohol and delocalisation back to the carbonyl oxygen) transfer the proton to make the hydroxylamine and then attack with amine. It's now 5-endo-tet(ish) so you've got the flexibility in the five membered ring now to position the amine for attack, make the five membered ring then another proton transfer to product....damn that mechanistic chemistry is rusty... - Cameron Neylon

I would expect the allylic carbocation should form in the presence of acid pretty easily. The question is - is that amide N nucleophilic enough to cyclize? Since you are making a 5 membered ring that isn't crazy to expect (although it might cyclize via the amide oxygen as well) - Jean-Claude Bradley

actually I remember a question like this in a workshop..."What do Baldwin's rules tell you about the cyclisation of the cyclisation of this nucleophile onto that carbocation to form a five membered ring?" Answer absolutely nothing because it is charged... :-) - Cameron Neylon

Cameron, I think we need to deprotonate, but we're in acid, so whaddya mean? (This making you nostalgic?) - Matthew Todd