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

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posted on 03.09.2018, 00:00 by Chaorong Qi, Youbin Peng, Lu Wang, Yanwei Ren, Huanfeng Jiang
A copper-catalyzed [2 + 3] formal cyclization reaction between α-hydroxyl ketones and arylacetonitriles has been developed. The reaction outcome was ultimately dependent on the structure of the α-hydroxy ketones employed. Tertiary α-hydroxy ketones gave 3,4,5,5-tetrasubstituted butenolides as the sole products, while secondary α-hydroxy ketones furnished 2,4,5-trisubstituted oxazoles selectively. This method has many advantages, such as the use of easily available substrates, broad substrate scope, good functional tolerance, and milder reaction conditions.