Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate
Organic Letters2001Vol. 3(23), pp. 3729–3732
Citations Over TimeTop 10% of 2001 papers
Chien‐Tien Chen, Jen‐Huang Kuo, Chun‐Hsin Li, Nivrutti B. Barhate, Sang‐Wen Hon, Tai-Wei Li, Shi‐Deh Chao, Chia-Cheng Liu, Ying-Chieh Li, I. L. Chang, Jin‐Sheng Lin, Chin-Jing Liu, Y. C. Chou
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.
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