1,3-Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: Scope, Limitations and Asymmetric Cycloadditions
2006 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 348, no 16-17, 2421-2430 p.Article in journal (Refereed) Published
The development of a diastereoselective 1,3-dipolar cycloaddition of carbonyl ylides and imines for the synthesis of alpha-hydroxy-beta-amino esters is described. The methodology is successfully applied to chiral alpha-methylbenzylimines affording enantiomerically pure syn-beta-amino alcohols, which is exemplified with a short asymmetric synthesis of the paclitaxel side-chain. The use of chiral Rh(11) carboxylate catalysts for the development of a catalytic enantioselective 1,3-dipolar cycloaddition is also described, affording syn-beta-amino alcohols in modest enantiomeric purity (e.r. up to 82:18).
Place, publisher, year, edition, pages
2006. Vol. 348, no 16-17, 2421-2430 p.
amino alcohols; asymmetric 1, 3-dipolar cycloadditions; carbenoids; carbonyl ylides; imines; multicomponent reactions
IdentifiersURN: urn:nbn:se:kth:diva-7404DOI: 10.1002/adsc.200600324ISI: 000242471700017ScopusID: 2-s2.0-33845293766OAI: oai:DiVA.org:kth-7404DiVA: diva2:12422
QC 201008172007-08-232007-08-232010-08-17Bibliographically approved