Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate
Journal
Organic Letters
Journal Volume
3
Journal Issue
23
Pages
3729-3732
Date Issued
2001
Author(s)
Chen, C. T.
Kuo, J. H.
Li, C. H.
Barhate, N. B.
Hon, S. W.
Li, T. W.
Chao, S. D.
Liu, C. C.
Li, Y. C.
Chang, I. H.
Lin, J. S.
Liu, C. J.
Chou, Y. C.
Abstract
[reaction--see text] Among four vanadyl species examined, vanadyl triflate was the most efficient catalyst to facilitate nucleophilic acyl substitution of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. By using mixed-anhydride technique, one can achieve oleate and peptide syntheses. In marked contrast to common metal triflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.
Type
journal article