Osmium Tetroxide Anchored to Porous Resins Bearing Residual Vinyl Groups: A Highly Active and Recyclable Solid for Asymmetric Dihydroxylation of Olefins

(Matrix Presented) OsO₄ was simply immobilized onto resins such as Amberlite XAD-4 or XAD-7 bearing residual vinyl groups. The resulting osmylated resins are air-stable, nonvolatile, and much easier to handle than their homogeneous counterpart (OsO₄). Moreover, the resin-bound OsO₄ exhibited excellent catalytic activity in the asymmetric dihydroxylation of olefins and was easily recovered and reused in five consecutive reactions without any significant decrease in product yield. Turnover time, however, was significantly increased for the fourth and fifth reactions.