Iron-Catalyzed Asymmetric Olefin cis-Dihydroxylation with 97 % Enantiomeric Excess

摘要

The rising number of pharmaceuticals with chiral centers has heightened the necessity to discover catalysts that provide asymmetric induction into the products of their respective reactions. In addition, stringent constraints on trace impurities allowed in the marketed pharmaceutical products make the use of catalysts composed of physiologically benign metal centers increasingly attractive. The cis-dihydroxylation of olefins has become an important chemical reaction in the design of pharmaceuticals and natural product synthesis because this reaction is both stereospecific and, through the use of the Sharpless asymmetric dihydroxylation (AD) mixes, enantiospecific. A potential disadvantage of the Sharpless procedure is the extraordinary toxicity associated with the osmium metal in the AD mixes.