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A regio- and stereodivergent route to all isomers of vic-amino alcohols
KTH, Superseded Departments, Chemistry.
2002 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 24, 8574-8583 p.Article in journal (Refereed) Published
Abstract [en]

Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

Place, publisher, year, edition, pages
2002. Vol. 67, no 24, 8574-8583 p.
Keyword [en]
aza-payne rearrangement, ring-opening reactions, stereoselective synthesis, asymmetric-synthesis, enantioselective synthesis, 1,2-amino alcohols, beta-amino, 7-membered lactams, organic-synthesis, efficient method
Identifiers
URN: urn:nbn:se:kth:diva-22088DOI: 10.1021/jo0262053ISI: 000179509400037OAI: oai:DiVA.org:kth-22088DiVA: diva2:340786
Note
QC 20100525Available from: 2010-08-10 Created: 2010-08-10Bibliographically approved

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