期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 45, 页码 14878-14882出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806883
关键词
alkynes; cyclizations; heterocycles; gold; nitrones
资金
- Ministry of Education [MOE 106N506CE1]
- Ministry of Science and Technology, Taiwan [MOST 107-3017-F-007-002]
The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with synselectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.
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