Journal
SYNTHESIS-STUTTGART
Volume 52, Issue 7, Pages 1047-1059Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690751
Keywords
asymmetric catalysis; heterocycles; Michael addition; organocatalysis-; phase-transfer catalysis
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Funding
- Estonian Ministry of Education and Research [IUT 19-32, IUT 19-9, IUT 20-14, PRG399, PUT 1468]
- Centre of Excellence in Molecular Cell Engineering [20142020.4.01.15-0013]
- ASTRA 'TUT Institutional Development Programme for 2016-2022' Graduate School of Functional Materials and Technologies [2014-2020.4.01.16-0032]
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An asymmetric phase-transfer-catalyzed N -alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.
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