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Application of (S,S)-Pentacycloundecane bis(4-Phenyloxazoline) as a Novel Chiral Ligand for Catalysis of the Asymmetric Diels-Alder Reaction of Cyclopentadiene with 3-Acryloyl-2-oxazolidinone
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
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2009 (English)In: South African Journal of Chemistry, ISSN 0379-4350, E-ISSN 1996-840X, Vol. 62, 60-U78 p.Article in journal (Refereed) Published
Abstract [en]

The synthesis of the novel C-1 symmetric (S,S)-pentacycloundecane bis(4-phenyloxazoline) ligand 5 and its evaluation as a chiral Lewis acid catalyst in the benchmark asymmetric Diels-Alder reaction between 3-acryloyloxazolidin-2-one (6) and cyclopentadiene (7) is reported. From the various metal salts screened the anhydrous magnesium perchlorate complex emerged as the best catalyst. The endo-cycloadduct product 8 was afforded in 81% enantiomeric excess with an endo:exo ratio of 98:2. An extensive screening of various metal ions as complexing agents was performed and is also reported.

Place, publisher, year, edition, pages
2009. Vol. 62, 60-U78 p.
Keyword [en]
Pentacycloundecane, oxazolines, chiral catalysis, Diels-Alder reaction
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-129007ISI: 000266702800013OAI: oai:DiVA.org:uu-129007DiVA: diva2:332434
Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved

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