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Stereoselective Synthesis of 2,3-Dihydropyrroles from Terminal Alkynes, Azides, and α,β-Unsaturated Aldehydes via N-Sulfonyl-1,2,3-triazoles

Tomoya Miura*, Takamasa Tanaka, Kentaro Hiraga, Scott G. Stewart and Masahiro Murakami*

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email: tmiurasbchem.kyoto-u.ac.jp, murakamisbchem.kyoto-u.ac.jp

T. Miura, T. Tanaka, K. Hiraga, S. G. Stewart, M. Murakami, J. Am. Chem. Soc., 2013, 135, 13652-13655.

DOI: 10.1021/ja407166r (free Supporting Information)



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Abstract

N-Sulfonyl-1,2,3-triazoles generate α-imino rhodium carbene complexes, which further react with α,β-unsaturated aldehydes to produce trans-2,3-disubstituted dihydropyrroles. The method can be successfully applied to a one-pot process starting from terminal alkynes.

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Key Words

2-Pyrrolines


ID: J48-Y2013