RSS-Feed abonnieren
DOI: 10.1055/s-2005-869917
Exo-Selective Enantioselective Nitrone Cycloaddition
Rezensent(en): Hisashi Yamamoto, Matthew BoxerPublikationsverlauf
Publikationsdatum:
20. Juli 2005 (online)
Key words
1,3-dipolar cycloaddition - nitrones - nickel
Significance
1,3-Dipolar cycloadditions of nitrones and olefins are excellent means for the construction of isoxazolidines as well as γ-amino alcohols. This paper describes a Ni(II) catalyst that provides exceedingly high exo-selectivity accompanied by excellent enantioselectivities with catalyst loadings as low as 5 mol%.
Comment
Chiral amino alcohols are important building blocks in many bio-active compounds. This communication is a standout example in that perfect exo-selectivity was obtained in many cases. The use of thiazolidinethiones as key substrates in the Binim-DCOH-Ni(II) (structure not known) catalyzed reaction also has interesting implications in the catalyst structure and function.