221048-56-2Relevant academic research and scientific papers
Formation of enantiopure β-amino alcohols with a 3-oxa-2,7- diazabicyclo[3.3.0]octane framework
Aurich, Hans Guenter,Soeberdt, Michael,Harms, Klaus
, p. 1249 - 1270 (2007/10/03)
N-Allylamino alcohols 11a-g were prepared from enantiopure (1S, 2S)-2- amino-1-phenylpropane-1,3-diol (8) by various reaction pathways. Selective Swern oxidation of the primary alcohol group of compounds 11 followed by treatment of the resulting aldehyde with N-alkylhydroxylamines afforded the corresponding nitrones that underwent an intramolecular 1,3-dipolar cycloaddition to give the bicyclic compounds 12 and 13. 12c and 13c (R3 = allyl) were deallylated providing compounds 12i and 13i, which could be methylated subsequently yielding 12k and 13k, respectively. X-ray analyses of 13a,c and 12g were performed indicating different conformations of 13a and c on the one hand and of 12g on the other hand. Conclusions concerning the conformation of the other compounds 12 and 13 were drawn from their 1H NMR data. Compounds 12 and 13 act as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde, however, the enantiomeric excess of the 1-phenylpropane-1-ol is usually low, the best result (79% ee) was achieved with compound 12c.
