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Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate

Chien-Tien Chen*, Jen-Huang Kuo, Chun-Hsin Li, N. B. Barhate, Sang-Wen Hon, Tai-Wei Li, Shi-Deh Chao, Chia-Cheng Liu, Ying-Chieh Li, I-Hsin Chang, Jin-Sheng Lin, Chin-Jing Liu, and Y-Chen Chou

*Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan, R.O.C. Email: ctchenmx.nthu.edu.tw

C.-T. Chen, J.-H. Kuo, C.-H. Li, N. B. Barhate, S.-W. Hon, T.-W. Li, S.-D. Chao, C.-C. Liu, Y.-C. Li, I.-H. Chang, J.-S. Lin, C.-J. Liu, Y.-C. Chou, Org. Lett., 2001, 3, 3729-3732.

DOI: 10.1021/ol016684c



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Abstract

Vanadyl triflate efficiently catalyzes a 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, oleate and peptide syntheses can be achieved.

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Key Words

acetates, pivalates, acylation


ID: J54-Y2001