Enantioselective organocatalysis using SOMO activation

Enamines, formed from the corresponding carbonyl compounds and appropriate chiral amine catalysts, can be oxidized to radical cation species. These radical cations can be intercepted by a range of SOMO-philic reagents, such as alkenes, arenes and some heteroatom based reagents. This methodology affo...

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Veröffentlicht in:New journal of chemistry 2016, Vol.4 (6), p.4855-4864
Hauptverfasser: Me iarová, Mária, Tisovský, Pavol, Šebesta, Radovan
Format: Artikel
Sprache:eng
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Zusammenfassung:Enamines, formed from the corresponding carbonyl compounds and appropriate chiral amine catalysts, can be oxidized to radical cation species. These radical cations can be intercepted by a range of SOMO-philic reagents, such as alkenes, arenes and some heteroatom based reagents. This methodology affords diversely substituted chiral carbonyl compounds. Organo-SOMO activation expanded the scope of enamine/iminium based organocatalytic transformations and it enables new reaction partners to be combined efficiently. Enantioselective organo-SOMO activation enables radical based functionalization of carbonyl compounds.
ISSN:1144-0546
1369-9261
DOI:10.1039/c6nj00079g