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Diastereoselective addition of chiral azomethine ylides to cyclic alpha,beta-unsaturated N-enoylbornanesultams
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
2002 (English)In: Journal of the Chemical Society. Perkin Transactions 1, ISSN 1472-7781, Vol. 2002, no 8, 1076-1081 p.Article in journal (Refereed) Published
Abstract [en]

Doubly diastereoselective 1,3-dipolar cycloaddition reactions of chiral non-racemic azomethine ylides to cyclic five-and six-membered α,β-unsaturated N-enoylbornanesultams were carried out. When suitable solvents were used, the fused bicyclic adducts formed were obtained in good diastereoselectivity. Moreover, a change of the absolute configuration of the starting ylide precursor reversed the diastereoselectivity of some such reactions. Cleavage of the chiral auxiliary of the cycloadducts furnished amino alcohols and a β-amino ester. The latter was transformed into a known precursor of an antibacterial compound.

Place, publisher, year, edition, pages
2002. Vol. 2002, no 8, 1076-1081 p.
Keyword [en]
1, 3-dipolar cycloaddition
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-4070DOI: 10.1039/b200579dISI: 000175001100010Scopus ID: 2-s2.0-0036010001Local ID: 4591OAI: oai:DiVA.org:miun-4070DiVA: diva2:29102
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-17Bibliographically approved

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CiteExportLink to record
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