Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 40, Pages 14250-14254Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908693
Keywords
Bronsted bases; 1; 6-conjugate additions; organocatalysis; synthetic methods; trienolates
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Funding
- University of the Basque Country UPV/EHU [UFI QOSYC 11/22]
- Basque Government (GV) [IT-1236-19]
- Ministerio de Economia y Competitividad (MEC), Spain [CTQ2016-78487-C2]
- GV for a fellowship
- European Funding Horizon 2020-MSCA [ITN-EJD CATMEC 14/06-721223]
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A catalyst-driven one-pot reaction sequence is developed for the enantio- and diastereoselective synthesis of tetrasubstituted cyclohexenes from simple unsaturated ketones or thioesters. The method involves a tertiary amine/squaramide-catalyzed alpha-selective addition of transiently generated trienolates to nitroolefins, subsequent base-catalyzed double bond isomerization, and an intramolecular (vinylogous) 1,6-addition reaction, a rare key carbocyclization step that proceeded with essentially perfect stereocontrol.
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