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A Stereocontrolled 1,2‐Addition Reaction of Tetrazoles with Alkyl Propiolates for the Synthesis of Highly Functionalized Enamines

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A stereocontrolled 1,2‐addition reaction of 1‐aryl‐1H‐tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines was developed. In the presence of silver oxide (Ag2O), the 1,2‐addition reaction generated (Z)‐N‐cyano enamines in good yields with exclusive formation of the Z‐isomers. Meanwhile, the 1,2‐addition reaction generated (E)‐N‐cyano enamines in the presence of Ag2O and potassium carbonate (K2CO3) with high stereoselectivity and yields.

Document Type: Research Article

DOI: http://dx.doi.org/10.1002/adsc.201200868

Affiliations: 1: Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, People's Republic of China 2: Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, People's Republic of China, phone: (+86)-561-380-2069, Fax: (+86)-561-309-0518

Publication date: March 11, 2013

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