Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2011 Sep 7;133(35):13782-5.
doi: 10.1021/ja206050b. Epub 2011 Aug 17.

Enantioselective α-arylation of carbonyls via Cu(I)-bisoxazoline catalysis

James S Harvey  1 , Scott P Simonovich, Christopher R Jamison, David W C MacMillan
Affiliations

Enantioselective α-arylation of carbonyls via Cu(I)-bisoxazoline catalysis

James S Harvey et al. J Am Chem Soc. .

Abstract

The enantioselective α-arylation of both lactones and acyl oxazolidones has been accomplished using a combination of diaryliodonium salts and copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable α-carbonyl benzylic stereocenters, a valuable synthon for the production of medicinal agents.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Proposed Mechanism for Carbonyl α-Arylation
See this image and copyright information in PMC

References

    1. For racemic α-arylation of carbonyl compounds using Pd catalysis see: Muratake H, Nakai H. Tetrahedron Lett. 1999;40:2355.Martín R, Buchwald SL. Angew Chem, Int Ed. 2007;46:7236.Vo GC, Hartwig JF. Angew Chem, Int Ed. 2008;47:2127.

    1. For asymmetric α-arylation of carbonyl compounds, see: García-Fortanet J, Buchwald SL. Angew Chem, Int Ed. 2008;47:8108.Taylor AM, Altman RA, Buchwald SL. J Am Chem Soc. 2009;131:9900.Liao X, Weng Z, Hartwig JF. J Am Chem Soc. 2008;130:195.Hartwig and Liu have constructed α-methine stereogenic centers using a chiral auxiliary: Liu X, Hartwig JF. J Am Chem Soc. 2004;126:5182.

    1. Alemán J, Cabrera S, Maerten E, Overgaard J, Jørgensen KA. Angew Chem, Int Ed. 2007;46:5520. - PubMed
    1. Dai X, Strotman NA, Fu GC. J Am Chem Soc. 2008;130:3302. - PubMed
    2. Lundin PM, Esquivias J, Fu GC. Angew Chem, Int Ed. 2009;48:154. - PMC - PubMed
    3. Lou S, Fu GC. J Am Chem Soc. 2010;132:1264. - PMC - PubMed
    4. Lundin PM, Fu GC. J Am Chem Soc. 2010;132:11027. - PMC - PubMed

    1. Allen AE, MacMillan DWC. J Am Chem Soc. 2011;133:4260.For examples of α-carbonyl arylation via SOMO catalysis see: Conrad JC, Kong J, Laforteza BN, MacMillan DWC. J Am Chem Soc. 2009;131:11640.

Publication types