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
. 2014 Dec 1;5(12):4840-4844.
doi: 10.1039/C4SC01327A.

Enantioselective Synthesis of Tetrahydroquinolines, Tetrahydroquinoxalines, and Tetrahydroisoquinolines via Pd-Catalyzed Alkene Carboamination Reactions

B A Hopkins  1 , J P Wolfe  1
Affiliations

Enantioselective Synthesis of Tetrahydroquinolines, Tetrahydroquinoxalines, and Tetrahydroisoquinolines via Pd-Catalyzed Alkene Carboamination Reactions

B A Hopkins et al. Chem Sci. .

Abstract

A catalyst composed of Pd2(dba)3 and (S)-Siphos-PE provides excellent results in Pd-catalyzed alkene carboamination reactions between aniline derivatives bearing pendant alkenes and aryl or alkenyl halides. These transformations generate tetrahydroquinolines and tetrahydroquinoxalines that contain quaternary carbon stereocenters with high levels of asymmetric induction. In addition this catalyst also effects the asymmetric synthesis of tetrahydroisoquinolines via related transformations of 2-allylbenzylamines. In contrast to most other approaches to the asymmetric synthesis of these compounds, which frequently involve functional group interconversion or a single C-C or C-N bond-forming event, the carboamination reactions generate both a C-N bond, a C-C bond, and a stereocenter.

PubMed Disclaimer

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. For a review on the synthesis and biological activity of tetrahydroquinolines, see: Sridharan V, Suryavanshi PA, Menéndez JC. Chem. Rev. 2011;111:7157. For reviews on the synthesis and biological activity of tetrahydroisoquinolines, see: Scott JD, Williams RM. Chem. Rev. 2002;102:1669. Bentley KW. Nat Prod. Rep. 2006;23:444. Chrzanowska M, Rozwadowska MD. Chem. Rev. 2004;104:3341. For reviews on the synthesis and biological activity of tetrahydroquinoxalines, see: Mamedov VA, Zhukova NA. Prog. Heterocycl. Chem. 2012;24:1. Mamedov VA, Zhukova NA. Prog. Heterocycl. Chem. 2012;24:55.

    1. Wang W-B, Lu S-M, Yang P-Y, Han X-W, Zhou Y-G. J. Am. Chem. Soc. 2003;125:10536. - PubMed
    2. Mršić N, Jerphagnon T, Minnaard AJ, Feringa BL, de Vries JG. Adv. Synth. Catal. 2009;351:2549.
    3. Shi L, Ye Z-S, Cao L-L, Guo R-N, Hu Y, Zhou Y-G. Angew. Chem., Int. Ed. 2012;51:8286. - PubMed
    4. Iimuro A, Yamaji K, Kandula S, Nagano T, Kita Y, Mashima K. Angew. Chem., Int. Ed. 2013;52:2046. - PubMed
    5. Rueping M, Antonchick AR, Theissmann T. Angew. Chem., Int. Ed. 2006;45:3683. - PubMed
    6. Rueping M, Tato F, Schoepke FR. Chem.-Eur. J. 2010;16:2688. - PubMed
    7. Cartigny D, Berhal F, Nagano T, Phansavath P, Ayad T, Genêt J-P, Ohshima T, Mashima K, Ratovelomanana-Vidal V. J. Org. Chem. 2012;77:4544. - PubMed

    1. For a recent review on asymmetric hydrogenation of heteroarenes see: Wang D-S, Chen Q-A, Lu S-M, Zhou Y-G. Chem. Rev. 2012;112:2557.

    1. Han Z-Y, Xiao H, Chen X-H, Gong L-Z. J. Am. Chem. Soc. 2009;131:9182. - PubMed
    2. Patil NT, Wu H, Yamamoto Y. J. Org. Chem. 2007;72:6577. - PubMed
    1. Okamoto S, Teng X, Fujii S, Takayama Y, Sato F. J. Am. Chem. Soc. 2001;123:3462. - PubMed
    2. Hashimoto T, Omote M, Maruoka K. Angew. Chem., Int. Ed. 2011;50:8952. - PubMed
    3. Shirakawa S, Liu K, Ito H, Le TN, Maruoka K. Adv. Synth. Catal. 2011;353:2614.

LinkOut - more resources