A New Twist on Cooperative Catalysis

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Science  31 May 2013:
Vol. 340, Issue 6136, pp. 1052-1053
DOI: 10.1126/science.1238769

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The stereochemical configuration of an organic compound is often linked directly to its physical and biological properties. Larger molecules can contain multiple stereochemical elements, and chiral catalysts are often used to control each of these defined spatial arrangements in the efficient synthesis of a complex target (1). Many powerful enantioselective catalysts, which control the handedness or absolute configuration of a product, have been developed (2), but full control of the relative configuration in compounds can be a greater challenge if multiple stereocenters are generated; high diastereoselectivity, where one relative configuration is established, may be achieved, but access to the complementary diastereomeric product usually requires major redesign of the catalyst, substrate, and/or reaction conditions, and in some cases is not possible at all (see the figure, panel A) (3). On page 1065 of this issue, Krautwald et al. (4) demonstrate an elegant solution to this challenge based on the cooperative action of multiple chiral catalysts in a single reaction.