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
. 2010 Nov 19;12(22):5112-5.
doi: 10.1021/ol102246d. Epub 2010 Oct 20.

Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation

Chunliang Lu  1 , Qing Xiao, Paul E Floreancig
Affiliations

Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation

Chunliang Lu et al. Org Lett. .

Abstract

Spirooxindole amides can be prepared by the intramolecular addition of functionalized indoles into acylimines that are accessed from nitriles by hydrozirconation and acylation. The stereochemical outcome at the quaternary center was controlled by the steric bulk of the substituent at the 2-position of the indole unit. The products are well-suited for diversification to prepare libraries.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Spirooxindole formation through acylimine addition.
Scheme 2
Scheme 2
Substrate synthesis.
Scheme 3
Scheme 3
Oxindole formation through nitrile hydrozirconation, acylation, and intramolecular addition.
Scheme 4
Scheme 4
Spirooxindole functionalizations.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Zhou F, Liu YL, Zhou J. Adv Synth Catal. 2010;352:1381.
    2. Galliford CV, Scheidt KA. Angew Chem Int Ed. 2007;46:8748. - PubMed
    3. Marti C, Carreira EM. Eur J Org Chem. 2003:2209.

    1. For selected recent examples, see: Zhang Y, Panek JS. Org Lett. 2009;11:3366.Shintani R, Hiyashi S-y, Murakami M, Takeda M, Hiyashi T. Org Lett. 2009;11:3754.Bencivenni G, Wu LY, Mazzanti A, Giannichi B, Pesciaioli F, Song MP, Bartoli G, Melchiorre P. Angew Chem Int Ed. 2009;48:7200.Chen XH, Wei Q, Luo SW, Xiao H, Gong LZ. J Am Chem Soc. 2009;131:13819.Liang B, Kalidindi S, Porco JA, Jr, Stephenson CRJ. Org Lett. 2010;12:572.Jiang K, Jia ZJ, Chen S, Wu L, Chen YC. Chem Eur J. 2010;16:2852.Viswambharan B, Selvakumar K, Madhavan S, Shanmugam P. Org Lett. 2010;12:2108.White JD, Li Y, Ihle DC. J Org Chem. 2010;75:3569.Jaegli S, Erb W, Retailleau P, Vors JP, Neuville L, Zhu J. Chem Eur J. 2010;16:5863.Chen WB, Wu ZJ, Pei QL, Cun LF, Zhang XM, Yuan WC. Org Lett. 2010;12:3132.

    1. Lo MMC, Neumann CS, Nagayama S, Perlstein EO, Schreiber SL. J Am Chem Soc. 2004;126:16077. - PubMed
    2. Chen C, Li X, Neumann CS, Lo MMC, Schreiber SL. Angew Chem Int Ed. 2005;44:2249. - PubMed
    1. Ding K, Lu Y, Nikolovska-Coleska Z, Qiu S, Ding Y, Gao W, Stuckey J, Krajewski K, Roller PP, Tomita Y, Parrish DA, Deschamps JR, Wang S. J Am Chem Soc. 2005;127:10130. - PubMed
    2. Yu S, Qin D, Shangary S, Chen J, Wang G, Ding K, McEachern D, Qiu S, Nikolovska-Coleska Z, Miller R, Kang S, Yang D, Wang S. J Med Chem. 2009;52:7970. - PMC - PubMed
    1. Rottmann M, McNamara C, Yeung BKS, Lee MCS, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, González-Páez G, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck HP, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT. Science. 2010;329:1175. - PMC - PubMed

Publication types