Journal
ORGANIC LETTERS
Volume 20, Issue 4, Pages 1256-1260Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00222
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Funding
- National Natural Science Foundation of China [21502089]
- Jiangsu Province Funds Surface Project [BK 20161541]
- Nanjing Tech University [39837107]
- Jiangsu National Synergetic Innovation Center for Advanced Materials through SICAM Fellowship
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A highly site-selective acyloxylation of stable enamines with PhI(OAc)(2) under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the alpha- or beta-site-selective product could be obtained with high selectivity. For the alpha-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.
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