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
. 2012 Feb 1;134(4):2020-3.
doi: 10.1021/ja211272v. Epub 2012 Jan 24.

Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular Heck-type coupling cascade

Timothy W Liwosz  1 , Sherry R Chemler
Affiliations

Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular Heck-type coupling cascade

Timothy W Liwosz et al. J Am Chem Soc. .

Abstract

Enantioselective copper-catalyzed cyclization of γ-alkenylsulfonamides and a δ-alkenylsulfonamide in the presence of a range of vinyl arenes results in variously functionalized 2-substituted chiral nitrogen heterocycles via a formal alkene C-H functionalization process. Application of this reaction to the concise synthesis of a 5-HT(7) receptor antagonist is demonstrated.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1
Alkene Amination–Heck-Type Coupling Cascade
Scheme 2
Scheme 2
Concise Synthesis of a 5-HT7 Receptor Antagonist
See this image and copyright information in PMC

References

    1. Recent examples: Ilies L, Asako S, Nakamura E. J Am Chem Soc. 2011;133:7672.Schomaker JM, Boyd WC, Stewart IC, Toste FD, Bergman RG. J Am Chem Soc. 2008;130:3777.Tsai AS, Brasse M, Bergman RG, Ellman JA. Org Lett. 2011;13:540.Rakshit S, Grohmann C, Besset T, Glorius F. J Am Chem Soc. 2011;133:2350.Shi BF, Zhang YH, Lam JK, Wang DH, Yu JQ. J Am Chem Soc. 2010;132:460.Hatamoto Y, Sakaguchi S, Ishii Y. Org Lett. 2004;6:4623.Xu YH, Lu J, Loh TP. J Am Chem Soc. 2009;131:1372.Yu H, Jin W, Sun C, Chen J, Du W, He S, Yu Z. Angew Chem, Int Ed. 2010;49:5792.

    1. Selected reviews: Oestrich M, editor. The Mizoroki-Heck Reaction. John Wiley & Sons; West Sussex, UK: 2009. Heck RF. Acc Chem Res. 1979;12:146.de Meijeres A, Meyer FE. Angew Chem, Int Ed. 1994;33:2379.Beletskaya IP, Cheprakov AV. Chem Rev. 2000;100:3009.Cu-catalyzed Heck-type reactions: Iyer S, Ramesh C, Sarkar A, Wadgaonkar PP. Tetrahedron Lett. 1997;38:8113.Li JH, Wang DP, Xie YX. Tetrahedron Lett. 2005;46:4941.Peng Y, Chen J, Liu M, Gao W, Wu H. Synthesis. 2011:213.

    1. Firmansjah L, Fu GC. J Am Chem Soc. 2007;129:11340. - PubMed
    2. Bloome KS, McMahen RL, Alexanian EJ. J Am Chem Soc. 2011;133:20146. - PubMed
    3. Stowers KJ, Fortner KC, Sanford MS. J Am Chem Soc. 2011;133:6541. - PMC - PubMed

    1. Heck-type couplings that proceed via alkyl radical intermediates: Branchaud BP, Detlefsen WD. Tetrahedron Lett. 1991;32:6273.Ikeda Y, Nakamura T, Yorimitsu H, Oshima K. J Am Chem Soc. 2002;124:6514.Terao J, Kambe N. Bull Chem Soc Jpn. 2006;79:663.Lebedev SA, Petrov ES, Beletskaya IP. J Organomet Chem. 1988;344:253.Song CX, Cai GX, Farrell TR, Jiang ZP, Li H, Gan LB, Shi ZJ. Chem Commun. 2009:6002.Furst L, Matsuura BS, Narayanam JMR, Tucker JW, Stephenson CRJ. Org Lett. 2010;12:3104.Weiss ME, Kreis LM, Lauber A, Carreira EM. Angew Chem, Int Ed. 2011;50:11125.

    1. Intermolecular additionof β-aminoalkyl radicals to alkenes has been demonstrated: Maria EJ, Da Silva AD, Fourrey JL, Machado AS, Robert-Gero M. Tetrahedron Lett. 1994;35:3301.

Publication types