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
. 2008 Mar 26;130(12):3736-7.
doi: 10.1021/ja710990d. Epub 2008 Mar 6.

Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes

Affiliations

Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes

David J Gorin et al. J Am Chem Soc. .

Abstract

Intermolecular annulation of enynes and propargyl esters to selectively produce styrenes or fluorenes is reported. The divergent arene syntheses involve a Au-catalyzed, two-pot, multistep process proceeding by cis-diastereoselective cyclopropanation, cycloisomerization, and, finally, annulation or elimination.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Proposed Mechanism for the Formation of 3 and 4.

References

    1. For a review, see: Saito S, Yamamoto Y. Chem. Rev. 2000;100:2901. Intramolecular annulation of enynes and alkynes: Dunetz JR, Danheiser RL. J. Am. Chem. Soc. 2005;127:5776. Danheiser RL, Gould AE, de la Pradilla RF, Helgason AL. J. Org. Chem. 1994;59:5514. Intramolecular annulation of arene-ynes and alkynes: Lian J-J, Chen P-C, Lin Y-P, Ting H-C, Liu R-S. J. Am. Chem. Soc. 2006;128:11372. Rodriguez D, Martinez-Esperon MF, Navarro-Vazquez A, Castedo L, Dominguez D, Saa C. J. Org. Chem. 2004;69:3842.

    1. Agenet N, Gandon V, Vollhardt KPC, Malacria M, Aubert C. J. Am. Chem. Soc. 2007;129:8860. - PubMed
    2. Chopade PR, Louie J. Adv. Synth. Catal. 2006;348:2307.
    1. Rubina M, Conley M, Gevorgyan V. J. Am. Chem. Soc. 2006;128:5818. - PubMed
    2. Saito S, Salter MM, Gevorgyan V, Tsuboya N, Tando K, Yamamoto Y. J. Am. Chem. Soc. 1996;118:3970.
    3. Gevorgyan V, Yamamoto Y. J. Organomet. Chem. 1999;576:232.
    1. Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007;107:3117. - PubMed
    1. Cyclopropanations of enynes are surprisingly undeveloped. Cyclopropanation with diazo-derived carbenes: Gmyzina RN, D'yakonov IA, Danilkina LP. Zhur. Obshch. Khimii. 1970;6:2168. Shapiro EA, Romanova TN, Dolgii IE, Nefedov OM. Izv. Akadem. Nauk SSSR, Seriya Khimicheskaya. 1985;11:2535. Kretschik O, Nieger M, Dotz KH. Chem. Ber. 1995;128:987. Simmons-Smith: Du H, Long J, Shi Y. Org. Lett. 2006;8:2827.

Publication types