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Comparison of Tetrahydroisoquinoline (TIQ) Thiazole and Oxazoline Ligands for Asymmetric Henry Reactions
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
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2012 (English)In: South African Journal of Chemistry, ISSN 0379-4350, E-ISSN 1996-840X, Vol. 65, 23-29 p.Article in journal (Refereed) Published
Abstract [en]

A series of novel C-1 symmetric thiazole ligands with a tetrahydroisoquinoline (TIQ) backbone were synthesized. Their application in the catalytic asymmetric Henry reaction was investigated with comparison to a corresponding TIQ oxazoline ligand. The Cu(II)-oxazoline complex was more reactive and furnished moderate enantioselectivities up to 61:36 (syn:anti) with 75:25 diastereomeric excess, while the Cu(II)-thiazole complexes had lower selectivity. This is the first example where a direct comparison between an N, N-type thiazole and oxazoline ligands has been studied.

Place, publisher, year, edition, pages
2012. Vol. 65, 23-29 p.
Keyword [en]
Tetrahydroisoquinoline, thiazole, oxazoline, Henry reaction, enantioselectivity
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-259779ISI: 000301284200005OAI: oai:DiVA.org:uu-259779DiVA: diva2:845423
Available from: 2015-08-11 Created: 2015-08-11 Last updated: 2017-12-04Bibliographically approved

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