Journals / Turkish Journal of Chemistry / 2013 / Cilt: 37 - Sayı: 4
Asymmetric synthesis of a-(heteroaryl)alkylamines and a -amino acids via nucleophilic 1,2-addition of lithiated heterocycles to aldehyde SAMP-hydrazones
- Journal
- Turkish Journal of Chemistry
- Pages
- 492–518
- DOI
- —
Abstract
The asymmetric synthesis of a-(heteroaryl)alkylamines was accomplished by employing a diastereoselective nucleophilic 1,2-addition of lithiated aromatic heterocycles to aldehyde SAMP-hydrazones, followed by BH3 . THF or SmI2 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 a-amino acids (ee = 90%--99%).
Özet
The asymmetric synthesis of a-(heteroaryl)alkylamines was accomplished by employing a diastereoselective nucleophilic 1,2-addition of lithiated aromatic heterocycles to aldehyde SAMP-hydrazones, followed by BH3 . THF or SmI2 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 a-amino acids (ee = 90%--99%).