Volume 89 Issue 7 | p. 35 | Concentrates
Issue Date: February 14, 2011

Acid Catalyst spurs Chiral Addition

A Brønsted acid’s attachment to an alkene controls selectivity, but by a different pathway than metal catalysts
Department: Science & Technology
Keywords: organocatalysis, acid, alkene, addition reaction, chiral

Add a new entry to the list of reactions that bulky proton donors can catalyze: asymmetric additions to carbon-carbon double bonds (Nature, DOI: 10.1038/nature09723). Researchers typically turn to chiral proton-donating Brønsted acids to functionalize carbonyl or other polar groups. Instead, F. Dean Toste and coworkers at the University of California, Berkeley, used a dithiophosphoric acid to turn dienes into chiral five-membered ring pyrrolidines and tetrahydrocarbazoles. The acid’s chiral counterion controls the . . .

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