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Tetrahydroisoquinoline-Based N-Oxides as Chiral Organocatalysts for the Asymmetric Allylation of Aldehydes
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
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2011 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2011, no 34, 6923-6932 p.Article in journal (Refereed) Published
Abstract [en]

The short synthesis of a series of novel chiral N-oxideorganocatalysts and their evaluation in the asymmetric allylation reaction of aromatic and α-β-unsaturated aldehydes with allyltrichlorosilane is reported. These readily modifiable organocatalysts are the first of their kind based on the tetrahydroisoquinoline framework. The chiral homoallyl products were obtained with good chemical efficiency (up to 93 % yield) and high enantioselectivity (up to 91 % ee) under mild reaction conditions (23 °C).

Place, publisher, year, edition, pages
2011. Vol. 2011, no 34, 6923-6932 p.
Keyword [en]
Organocatalysis, Allylation, Heterocycles, Aldehydes, Lewis bases, Tetrahydroisoquinoline
National Category
Organic Chemistry
Research subject
Organic Pharmaceutical Chemistry
URN: urn:nbn:se:uu:diva-165365DOI: 10.1002/ejoc.201100923ISI: 000297205800013OAI: oai:DiVA.org:uu-165365DiVA: diva2:473135
Available from: 2012-01-05 Created: 2012-01-05 Last updated: 2012-01-10Bibliographically approved

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Arvidsson, Per I
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