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1.1.6 Ketamination of Alkenes

DOI: 10.1055/sos-SD-201-00002

Muñiz, K.Science of Synthesis: Stereoselective Synthesis, (2011150.

This reaction represents the direct conversion of alkenes 37 into 2-amino ketones 38 (Scheme 30).[‌123‌] It is a side reaction of the aminohydroxylation reaction that takes place in the absence of the cinchona alkaloid ligand, presumably due to a diminished rate in cleavage of the intermediary osmaazaglycolate esters.[‌124‌] As a result, the transformation gives rise to racemic products. It is related to the previously discussed ruthenium-catalyzed ketohydroxylation reaction. As in ketohydroxylation, a reaction starting from enantiomerically pure amino alcohols from the asymmetric aminohydroxylation reaction, using the reaction conditions of osmium catalysis allows for clean transformation into the corresponding optically active 2-amino ketones within a two-step transformation.

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