The first is an interesting Nazarov cyclization followed by a Wagner-Meerwein rearrangement reported by Alison Frontier. Depending on the substitution, the path of the Nazarov is altered and the reaction is terminated by either a hydride shift or an aryl shift. Interesting paper well worth reading the details.
Jie Huang and Alison J. Frontier, JACS DOI: 10.1021/ja0716148
Mukund Sibi reported a novel organocatalytic method for the conjugate addition of hydroxylamines. The catalyst provides for both hydrogen bonding activation of the substrate and hydrogen bond-directivity for the incoming nucleophile.
Mukund P. Sibi and Kennosuke Itoh, JACS DOI: 10.1021/ja071739c
7 comments:
Greg, if you see prof Sibi you can suggest to him that one way to increase the reaction rate (or reduce the catalyst loading) would be to increase electron density on the hydroxylamine. I would suggest using p-MeO-benzylamine instead of BnONH2. Also meta-bis(trifluoromethyl)-benzene looks like a promising solvent for this reaction, it has a reasonable boiling point (115C) and is becoming reasonably cheap. I bough a 0.5kg bottle from Matrix for $55.
sorry for the typo, should have been O-(p-methoxybenzyl)-hydroxylamine, PMB-ONH2
Hey what? did you take another vacation??
I need more Carbon Tet!!!
Javaslinger
As a matter of fact, I have been on the road and am leaving again. Vacation? I wish. Anyway, I'll try to update from the road this week.
Thanks for the prodding!
Hey, when are you coming back? Been a long time. Everything ok?
i go to rochester, and i just recently saw jie defend. that paper is def. worth the read.
Jie defend? She was a postdoc for god's sake.
Post a Comment