148759-64-2Relevant articles and documents
Synthesis of Homochiral 3-Oxa-2,7-diazabicyclooctanes from Amino Acids by Intramolecular 1,3-Dipolar Cycloaddition of Nitrones
Aurich, Hans Guenter,Frenzen, Gerlinde,Gentes, Christian
, p. 787 - 796 (2007/10/02)
N-Allylamino alcohols 9 were prepared from amino acids by various methods.Swern oxidation of 9 afforded aldehydes 11.By reaction of 11 with N-alkylhydroxylamines nitrone intermediates 4 were formed which spontaneously underwent an intramolecular 1,3-dipolar cycloaddition to yield the bicyclic compounds 6.The cycloaddition proceeds diastereoselectively furnishing homochiral compounds 6 from homochiral starting materials.The structure of 6aA was confirmed by X-ray structural analysis. Key Words: Heterobicyclooctanes, homochiral / Amino acids / Nitrones / Cycloadditions, diastereoselective, intramolecular