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Science 3 February 2006:
Vol. 311. no. 5761, p. 573
DOI: 10.1126/science.311.5761.573g
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This Week in Science
The selective addition of hydrogen across carbon-carbon double bonds to generate homochiral products is used to prepare a wide range of compounds, both in the lab and in industry. However, the scope of this reaction is often limited by the need for a specific group adjacent to the olefin, whether a phenyl or a coordinating oxygen or nitrogen substituent, to direct the catalyst. Bell et al. (p. 642, published online 8 December 2005; see the Perspective by Wills) show that a class of iridium compounds, coordinated by chiral ligands with both phosphinite and pyridine groups, can catalyze the asymmetric hydrogenation of olefins bearing only simple alkyl substituents. They reduce a vitamin E precursor at two noncontiguous C=C bonds in an alkyl chain with net selectivity exceeding 98%.
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