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
Revue
Advanced Synthesis & Catalysis
Volume
358
Ticket
21
Pagination
3362–3367
Soumis le 7 septembre 2022