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.aleman
uam.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
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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
