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Science 27 July 2007:
Vol. 317. no. 5837, pp. 496 - 499
DOI: 10.1126/science.1145229
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Reports

A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis

Gregory L. Hamilton, Eun Joo Kang, Miriam Mba, F. Dean Toste*

Traditionally, transition metal–catalyzed enantioselective transformations rely on chiral ligands tightly bound to the metal to induce asymmetric product distributions. Here we report high enantioselectivities conferred by a chiral counterion in a metal-catalyzed reaction. Two different transformations catalyzed by cationic gold(I) complexes generated products in 90 to 99% enantiomeric excess with the use of chiral binaphthol–derived phosphate anions. Furthermore, we show that the chiral counterion can be combined additively with chiral ligands to enable an asymmetric transformation that cannot be achieved by either method alone. This concept of relaying chiral information via an ion pair should be applicable to a vast number of metal-mediated processes.

Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720, USA.

* To whom correspondence should be addressed. E-mail: fdtoste{at}berkeley.edu

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THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
A porphyrin complex of Gold(I): (Phosphine)gold(I) azides as cation precursors.
D. V. Partyka, T. J. Robilotto, M. Zeller, A. D. Hunter, and T. G. Gray (2008)
PNAS 105, 14293-14297
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Science. ISSN 0036-8075 (print), 1095-9203 (online)