Organo‐ and Iron(0) Catalysis for an Enantioselective Michael Addition–Hemiketalization–Fragmentation Sequence to Protected ω‐Hydroxy‐nitroketones

Abstract

AbstractBy 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.magnified image