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Catalytic asymmetric carbon-carbon bond forming reactions catalyzed by tetrahydroisoquinoline (TIQ) N,N '-dioxide ligands
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
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2013 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 24, no 4, 191-195 p.Article in journal (Refereed) Published
Abstract [en]

The use of TIQ-N,N'-dioxide ligands in asymmetric C-C bond forming reactions is described. In the Michael addition of cyclohexane-1,3-dione and malonates to beta,gamma-unsaturated alpha-ketoesters, excellent yields (up to 93%) and moderate to good enantioselectivities (70-89% ee) were obtained. The catalytic hetero-ene reaction of 2-methoxypropene with phenylglyoxal gave the ene product in excellent yield (95%) with moderate enantioselectivity (77% ee). The catalyst system performed well at temperatures ranging from 0 to 30 degrees C and relatively low catalyst loading (0.2-5 mol %) with dichloromethane being the preferred solvent for all reactions.

Place, publisher, year, edition, pages
2013. Vol. 24, no 4, 191-195 p.
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Natural Sciences
URN: urn:nbn:se:uu:diva-198404DOI: 10.1016/j.tetasy.2013.01.004ISI: 000316167800006OAI: oai:DiVA.org:uu-198404DiVA: diva2:616076
Available from: 2013-04-15 Created: 2013-04-15 Last updated: 2013-04-15Bibliographically approved

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Tetrahedron: asymmetry
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