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Perveen S, Zhao Z, Zhang G, et al. Enantioselective Synthesis of 1,2-Dihydronaphthalenes via Oxidative N-Heterocyclic Carbene Catalysis. Org Lett. 2017;19(10):2470-2473doi: 10.1021/acs.orglett.7b00555.
Perveen, S., Zhao, Z., Zhang, G., Liu, J., Anwar, M., & Fang, X. (2017). Enantioselective Synthesis of 1,2-Dihydronaphthalenes via Oxidative N-Heterocyclic Carbene Catalysis. Organic letters, 19(10), 2470-2473. https://doi.org/10.1021/acs.orglett.7b00555
Perveen, Saima, et al. "Enantioselective Synthesis of 1,2-Dihydronaphthalenes via Oxidative N-Heterocyclic Carbene Catalysis." Organic letters vol. 19,10 (2017): 2470-2473. doi: https://doi.org/10.1021/acs.orglett.7b00555
Perveen S, Zhao Z, Zhang G, Liu J, Anwar M, Fang X. Enantioselective Synthesis of 1,2-Dihydronaphthalenes via Oxidative N-Heterocyclic Carbene Catalysis. Org Lett. 2017 May 19;19(10):2470-2473. doi: 10.1021/acs.orglett.7b00555. Epub 2017 May 09. PMID: 28485600.
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Org Lett. 2017 May 19;19(10):2470-2473. doi: 10.1021/acs.orglett.7b00555. Epub 2017 May 09.

Enantioselective Synthesis of 1,2-Dihydronaphthalenes via Oxidative N-Heterocyclic Carbene Catalysis.

Organic letters

Saima Perveen, Zhifei Zhao, Guoxiang Zhang, Jian Liu, Muhammad Anwar, Xinqiang Fang

Affiliations

  1. State Key Laboratory of Structural Chemistry and Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences , Fuzhou 350100, China.

PMID: 28485600 DOI: 10.1021/acs.orglett.7b00555

Abstract

1,2-Dihydronaphthalenes are important molecules in both medicinal and synthetic chemistry, but methods for the catalytic asymmetric construction of this class of molecules are limited. The diastereo- and enantioselective N-heterocyclic carbene-catalyzed cascade annulation reactions using benzodiketones and enals under oxidative conditions, which afford a variety of 1,2-dihydronaphthalenes with two adjacent stereocenters in up to 99% yield, with >20:1 dr, and up to 99% ee, are reported. Furthermore, the product can be easily transformed to a series of useful compounds such as alcohol, amide, and epoxide.

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