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Asymmetric Synthesis of Rauhut-Currier type Products by a Regioselective Mukaiyama Reaction under Bifunctional Catalysis

María Frias, Rubén Mas-Ballesté, Saira Arias, Cuauhtemoc Alvarado and José Alemán*

*Department of Organic Chemistry (module 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Email: Jose.alemanuam.es

M. Frias, R. Mas-Ballesté, S. Arias, C. Alvarado, J. Alemán, J. Am. Chem. Soc., 2017, 139, 672-679.

DOI: 10.1021/jacs.6b07851 (free Supporting Information)


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Abstract

A bifunctional organocatalyst enables a 1,3-addition of silyl-dienol ethers to nitroalkenes to provide Rauhut-Currier type products with tri- and tetrasubstituted double bonds. The process takes place under smooth, nonanionic conditions, and with high enantiomeric excess. A rational mechanistic pathway is presented based on DFT and mechanistic experiments.

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proposed mechanism



Key Words

enones, nitro compounds, organocatalysis


ID: J48-Y2017