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- Title
One-Pot Enantioselective Synthesis of 1,4-Naphthoquinone-Derived Polycycles through Oxidative Dearomatization and Aminocatalysis.
- Authors
Pantaine, Loïc; Coeffard, Vincent; Moreau, Xavier; Greck, Christine
- Abstract
A synthetic process merging oxidative dearomatization and asymmetric aminocatalysis in a single vessel is reported. The PhI(OAc)2-mediated oxidation of 1,4-dihydroxynaphthalene is followed by a trienamine-mediated Diels-Alder cycloaddition/aldol reaction or a trienamine-mediated Diels-Alder cycloaddition/oxidation sequence depending on the dienal substitution pattern. The polycyclic compounds are obtained in good yields with enantiomeric excesses up to 99 %. Additionally, these polycyclic architectures can be synthesized with similar enantioselectivities through an unprecedented one-pot marriage of bodipy-photocatalyzed oxidative dearomatization of 1-naphthol and asymmetric aminocatalysis. A catalytic cycle is suggested to explain the reaction outcome.
- Subjects
ENANTIOSELECTIVE catalysis; CATALYSIS synthesis; ALDOLS; ENANTIOMERS; RING formation (Chemistry); OXIDATION
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 9, p2005
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403597