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
. 2015 Apr 15;137(14):4666-9.
doi: 10.1021/jacs.5b02316. Epub 2015 Apr 6.

Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines

Affiliations

Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines

Erhad Ascic et al. J Am Chem Soc. .

Abstract

A diastereo- and enantioselective CuH-catalyzed method for the preparation of highly functionalized indolines is reported. The mild reaction conditions and high degree of functional group compatibility as demonstrated with substrates bearing heterocycles, olefins, and substituted aromatic groups, renders this technique highly valuable for the synthesis of a variety of cis-2,3-disubstituted indolines in high yield and enantioeselectivity.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Proposed catalytic cycle for CuH-catalyzed synthesis of 2,3-disubstituted indolines.

References

    1. For selected examples, see:

    2. Crich D.; Banerjee A. Acc. Chem. Res. 2007, 40, 151. - PubMed
    3. Triggle D. J.; Mitchell J. M.; Filler R. CNS Drug Reviews 1998, 4, 87.
    4. Deutsch H. F.; Evenson M. A.; Drescher P.; Sparwasser C.; Madsen P. O. J. Pharm. Biomed. Anal. 1994, 12, 1283. - PubMed
    5. Silvestri R. J. Med. Chem. 2013, 56, 625. - PubMed
    6. Greig N. H.; Pei X.-F.; Soncrant T. T.; Ingram D. K.; Brossi A. Med. Res. Rev. 1995, 15, 3. - PubMed
    7. Neelamegam R.; Hellenbrand T.; Schroeder F. A.; Wang C.; Hooker J. M. J. Med. Chem. 2014, 57, 1488. - PMC - PubMed
    1. Podoll J. D.; Liu Y.; Chang L.; Walls S.; Wang W.; Wang X. Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 15573. - PMC - PubMed
    2. Poondra R. R.; Kumar N. N.; Nijian K.; Prakesch M.; Slater-Campagna V.; Reayi A.; Reddy T. P.; Choudhry A.; Barnes M. L.; Leek D. M.; Daroszewska M.; Lougheed C.; Xu B.; Schapira M.; Alaoui-Jamali M. A.; Arya P. J. Comb. Chem. 2009, 11, 303. - PubMed
    3. Gan Z. P.; Reddy T.; Quevillon S.; Couve-Bonnaire S.; Arya P. Angew. Chem., Int. Ed. 2005, 44, 1366. - PubMed
    1. For recent reviews, see:

    2. Liu D.; Zhao G.; Xiang L. Eur. J. Org. Chem. 2010, 3975.
    3. Zhang D.; Song H.; Qin Y. Acc. Chem. Res. 2011, 44, 447. - PubMed
    1. Wang D.-S.; Chen Q.-A.; Li W.; Yu C.-B.; Zhou Y.; Zhang X. J. Am. Chem. Soc. 2010, 132, 8909. - PubMed
    2. Duan Y.; Chen M.-W.; Chen Q.-A.; Yu C.-B.; Zhou Y.-G. Org. Biomol. Chem. 2012, 10, 1235. - PubMed
    3. Duan Y.; Chen M.-W.; Ye Z.-S.; Wang D.-S.; Chen Q.-A.; Zhou Y.-G. Chem.—Eur. J. 2011, 17, 7193. - PubMed
    4. Wang D.-S.; Tang J.; Zhou Y.-G.; Chen M.-W.; Yu C.-B.; Duan Y.; Jiang G.-F. Chem. Sci. 2011, 2, 803.
    5. Li C.; Chen J.; Fu G.; Liu D.; Liu Y.; Zhang W. Tetrahedron 2013, 69, 6839.
    6. Duan Y.; Li L.; Chen M.-W.; Yu C.-B.; Fan H.-J.; Zhou Y.-G. J. Am. Chem. Soc. 2014, 136, 7688. - PubMed
    7. Xiao Y.-C.; Wang C.; Yao Y.; Sun J.; Chen Y.-C. Angew, Chem. Int. Ed. 2011, 50, 10661. - PubMed
    1. Arp F. O.; Fu G. C. J. Am. Chem. Soc. 2006, 128, 14264. - PMC - PubMed
    2. Lopez-Iglesias M.; Busto E.; Gotor V.; Gotor-Fernández V. J. Org. Chem. 2012, 77, 8049. - PubMed
    3. Saito K.; Shibata Y.; Yamanaka M.; Akiyama T. J. Am. Chem. Soc. 2013, 135, 11740. - PubMed

Publication types

LinkOut - more resources