Organo- and Iron(0) Catalysis for an Enantioselective Michael Addition–Hemiketalization–Fragmentation Sequence to Protected omega-Hydroxy-nitroketones
By combining an organocatalyzed Michael addition of 1,3-diketones to hydroxy-nitroolefins with a subsequent, innovative iron(0)-catalyzed fragmentation, key enantioenriched ketones possessing additional nitro and protected alcohol functions could efficiently be prepared under excellent enantiocontrol (typically 95% ee). The reaction was made possible by the discovery that photochemical activation of iron pentacarbonyl [Fe(CO)5], a cheap widely available complex, efficiently catalyzed a Claisen-type fragmentation under mild conditions, avoiding decomposition of the intermediates and products.
Références
- Titre
- Organo- and Iron(0) Catalysis for an Enantioselective Michael Addition–Hemiketalization–Fragmentation Sequence to Protected omega-Hydroxy-nitroketones
- Type de publication
- Article de revue
- Année de publication
- 2016
- Auteurs
- Quintard, Adrien, and Rodriguez Jean
- Revue
- Advanced Synthesis & Catalysis
- Volume
- 358
- Ticket
- 21
- Pagination
- 3362–3367
Soumis le 7 septembre 2022