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Asymmetric conjugate addition of thioglycolate to a range of chalcones using tetrahydroisoquinoline (TIQ) N,N '-dioxide ligands
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2012 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 23, no 8, 616-622 p.Article in journal (Refereed) Published
Abstract [en]

A series of novel TIQ based N,N'-oxide ligands were synthesised and screened for their catalytic activity in the enantioselective conjugate addition of thioglycolate to chalcones. Bulky groups on the side chain of the TIQ backbone provided the highest enantioselectivity of up to 88% with 10 mol % catalyst loading. It was also observed that these reactions proceeded optimally in the presence of dichloromethane as a solvent. Screening of various metals emphasized La(OTf)(3) as the ideal pre-catalyst for this particular reaction.

Place, publisher, year, edition, pages
2012. Vol. 23, no 8, 616-622 p.
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Organic Chemistry
URN: urn:nbn:se:uu:diva-187794DOI: 10.1016/j.tetasy.2012.04.010ISI: 000306304200014OAI: oai:DiVA.org:uu-187794DiVA: diva2:575626
Available from: 2012-12-10 Created: 2012-12-10 Last updated: 2015-05-25Bibliographically approved

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Arvidsson, Per I.
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Organic Pharmaceutical Chemistry
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