Asymmetric synthesis of \alpha-(heteroaryl)alkylamines and \alpha -amino acids via nucleophilic 1,2-addition of lithiated heterocycles to aldehyde SAMP-hydrazones

Authors

DIETER ENDERS
GIUSEPPE DEL SIGNORE
GERHARD RAABE

DOI

10.3906/kim-1302-71

Abstract

The asymmetric synthesis of \alpha-(heteroaryl)alkylamines was accomplished by employing a diastereoselective nucleophilic 1,2-addition of lithiated aromatic heterocycles to aldehyde SAMP-hydrazones, followed by BH_3 . THF or SmI_2 promoted removal of the chiral auxiliary. The CBz or benzoyl-protected amines were obtained in good yields (40\%--78\%) and excellent enantiomeric excesses (ee = 88\%--99\%). The methodology can be applied to the synthesis of highly enantioenriched \alpha-amino acids (ee = 90\%--99\%).

Keywords

Amines, asymmetric synthesis, SAMP-hydrazone, nucleophilic addition, amino acids

First Page

492

Last Page

518

Recommended Citation

ENDERS, DIETER; SIGNORE, GIUSEPPE DEL; and RAABE, GERHARD (2013) "Asymmetric synthesis of \alpha-(heteroaryl)alkylamines and \alpha -amino acids via nucleophilic 1,2-addition of lithiated heterocycles to aldehyde SAMP-hydrazones," Turkish Journal of Chemistry: Vol. 37: No. 4, Article 3. https://doi.org/10.3906/kim-1302-71
Available at: https://journals.tubitak.gov.tr/chem/vol37/iss4/3