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Copper-Catalyzed [2 + 3] Cyclization of α-Hydroxyl Ketones and Arylacetonitriles: Access to Multisubstituted Butenolides and Oxazoles

Chaorong Qi*, Youbin Peng, Lu Wang, Yanwei Ren, Huanfeng Jiang*

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, People's Republic of China, Email: crqiscut.edu.cn, jianghfscut.edu.cn

C. Qi, Y. Peng, L. Wang, Y. Ren, H. Jiang, J. Org. Chem., 2018, 83, 11926-11935.

DOI: 10.1021/acs.joc.8b01822 (free Supporting Information)


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Abstract

A mild copper-catalyzed [2 + 3] formal cyclization reaction between α-hydroxyl ketones and arylacetonitriles provides butenolides or oxazoles depending on the structure of the α-hydroxy ketones employed. Whereas tertiary α-hydroxy ketones furnished 3,4,5,5-tetrasubstituted butenolides selectively, secondary α-hydroxy ketones gave 2,4,5-trisubstituted oxazoles as the sole products.

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Key Words

butenolides


ID: J42-Y2018