The direct osmylation reaction of allene is known to be inefficient and impractical mostly due to the low selectivity and low catalyst turn over. Here we describe a novel allene osmylation procedure. With the assistance of an electrophilic additive, the rate of allene oxidation by catalytic osmium tetroxide is significantly enhanced. A multi-component coupling reaction for converting di- and trisubstituted allenes to highly functionalized hydroxyketone is also realized.

Catalytic allene osmylation promoted by electrophile

244th National Meeting (2012)

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