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03/23/12

Nature Article: Synthesis in tight pockets: Highly selective synthesis of pheromones by new chiral acids

Nature Article: Synthesis in tight pockets: Highly selective synthesis of pheromones by new chiral acids

 

The sex pheromone olean of the olive fruit fly has the interesting property that one mirror image variant is active on males and the other one on females. Olean contains as the only source of chirality a so called spiroacetal, which can be selectively constructed by enzymes. However until today, chemists had been unable to mimic such enzymatic action. Now, new chiral acids have been designed by I. Čorić and B. List that catalyze selective spiroacetalisations, including one to furnish olean with remarkably high selectivity. A distinctive characteristic of these artificial catalysts is an extremely tight chiral pocket, reminiscent of those found in nature’s enzymes.
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