期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 4, 页码 1213-1217出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201810798
关键词
acyl radicals; organocatalysis; photochemistry; stereodivergence; Stetter reaction
资金
- MINECO [CTQ2016-75520-P]
- European Research Council [ERC 681840-CATA-LUX]
- CONACyT (Consejo Nacional de Ciencia y Tecnologia, Mexico) [237346]
We report a visible-light-mediated organocatalytic strategy for the enantioselective acyl radical conjugate addition to enals, leading to valuable 1,4-dicarbonyl compounds. The process capitalizes upon the excited-state reactivity of 4-acyl-1,4-dihydropyridines that, upon visible-light absorption, can trigger the generation of acyl radicals. By means of a chiral amine catalyst, iminium ion activation of enals ensures a stereoselective radical trap. We also demonstrate how the combination of this acylation process with a second catalyst-controlled bond-forming event allows to selectively access the full matrix of all possible stereoisomers of the resulting 2,3-substituted 1,4-dicarbonyl products.
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