期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 33, 页码 9788-9792出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604201
关键词
asymmetric synthesis; chiral phosphoric acids; nitrogen heterocycles; organocatalysis; ortho-quinone methide imines
资金
- Deutsche Forschungsgemeinschaft [SCHN 441/11-1]
- Deutsche Bundesstiftung Umwelt (DBU)
- DAAD
The direct and highly enantioselective synthesis of tetrahydroacridines was achieved through the phosphoric acid catalyzed addition of enamides to in situ generated orthoquinone methide imines and subsequent elimination. This novel one-step process constitutes a very efficient, elegant, and selective synthetic approach to valuable N-heterocycles with a 1,4-dihydroquinoline motif. By subsequent highly diastereo-selective hydrogenation and N-deprotection the reaction products were easily converted into free hexahydroacridines with a total of three new stereogenic centers.
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