Work

A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis

Year: 2007

Type: article

Abstract: 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.

Source: Science

DOI: 10.1126/science.1145229

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

Institution: University of California, Berkeley

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Catalytic Methods for Carbon-Carbon and Carbon-Heteroatom Bond Formation