期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 40, 页码 10768-10773出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406100
关键词
anhydrides; cyclization; organocatalysis; phosphorus; zwitterions
资金
- Shanghai Municipal Committee of Science and Technology [11JC1402600]
- National Basic Research Program of China (973) [2010CB833302]
- National Natural Science Foundation of China [20472096, 21372241, 21361140350, 20672127, 21102166, 21121062, 21302203, 20732008]
A novel phosphine-catalyzed [4+1] annulation of maleimides with 4,4-dicyano-2-methylenebut-3-enoates has been developed to afford spirocyclic products, and the maleimides serves as C-1 synthons. Moreover, a phosphinecatalyzed formal [3+2] annulation between 4,4-dicyano-2-methylenebut-3-enoates and maleic anhydride has been also achieved, and maleic anhydride behaved as a C-3 synthon in the reaction, thus efficiently affording the functionalized cyclopentenones. A stable phosphinium-containing zwitterionic compound is the key reactive intermediate in both annulations and was successfully isolated. Plausible mechanisms have been proposed on the basis of control experiments and deuterium-labeling experiments.
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