期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 41, 页码 12697-12701出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706304
关键词
aldehydes; amines; heterocycles; ketimines; organocatalysis
资金
- NSFC [21372193, 21362040, 21672184]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT13095]
- University of Yunnan Province
The application potential of primary amine catalysts in the context of Mannich reactions of aldehydes with ketimines is exemplified by isatin-derived ketimines and cyclic trifluoromethyl ketimines. Primary amine catalysts exhibit either unusual stereoselectivity or reactivity, which is not observable with secondary amine catalysts. Moreover, reversal of diastereofacial selectivity between primary and secondary amine catalysts is disclosed. These new reactions provide useful methods for the syntheses of chiral 3-substituted 3-amino-2-oxindoles and dihydroquinazolinones bearing a trifluoromethylated quaternary stereocenter. The synthetic utility of the reactions is demonstrated through the formal synthesis of AG-041R and DPC 083 and the total synthesis of (-)-psychotriasine.
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