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A New Multicomponent Reaction Catalyzed by a [Lewis Acid]+[Co(CO)4]- Catalyst:  Stereospecific Synthesis of 1,3-Oxazinane-2,4-diones from Epoxides, Isocyanates, and CO
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
2007 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, Vol. 129, no 26, 8156-8162 p.Article in journal (Refereed) Published
Abstract [en]

The use of mechanistic information to develop a new, catalytic multicomponent reaction is described. The complex [(salph)Al(THF)2+[co(CO)4]-(1, salph = N,N-o-phenylenebis(3,5-di-tert-butylsalicylideneimine), THF = tetrahydrofuran), wich is known to carbonylate epoxides, aziridines, and B-lactones, was used to catalyze the synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO. Under optimized conditions, the reaction was both selective and high-yielding. 1,3-Oxazinane-2,4-diones were synthesized from a variety of epoxides and isocyanates, including some epoxides that do not undergo simple ring-expansion carbonylation. The best results were obtained using highly electrophilic isocyanates. The mechanism of the multicomponent reaction was investigated using labeling and stereochemsitry, and the data obtained were consistent with the 1-catalyzed formation of B-lactone and 1,3-oxazinane-2,4-dione from a common intermediate.

Place, publisher, year, edition, pages
2007. Vol. 129, no 26, 8156-8162 p.
National Category
Chemical Sciences
URN: urn:nbn:se:uu:diva-11241DOI: 10.1021/ja069065dOAI: oai:DiVA.org:uu-11241DiVA: diva2:39009
Available from: 2007-06-28 Created: 2007-06-28Bibliographically approved

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Church, Tamara
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