A regio- and stereodivergent route to all isomers of vic-amino alcohols
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
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.
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-122406DOI: 10.1021/jo0262053ISI: 000179509400037OAI: oai:DiVA.org:su-122406DiVA: diva2:866069