Clean, Green Chiral Reactions—Just Add a Salt

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Science  11 Jun 2010:
Vol. 328, Issue 5984, pp. 1365-1366
DOI: 10.1126/science.1191408

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Chirality—literally handedness—refers to the mirror-image, or left-right asymmetry of objects like shoes and gloves. Like our hands, many chemical compounds (and most biomolecules) exist as enantiomers, which, relative to each other, have mirror-image arrangements of substituents around an atom (typically carbon or nitrogen). In many cases, pharmaceuticals must have a specific chirality in order to be active, but making pure chiral compounds is difficult and costly. Traditionally, chemists have relied on reagents for controlling chirality that contain heavy metals (1), the presence of which can lead to toxicity issues. A relatively new alternative is the use of nonmetal catalysts called organocatalysts. On page 1376 of this issue, Uyanik et al. (2) report a more “green” organocatalytic reaction that also uses an iodine reagent to closes rings in a molecule during an oxidation step.