- Turkish Journal of Chemistry
- Vol: 37 Issue: 4
- Asymmetric synthesis of a-(heteroaryl)alkylamines and a -amino acids via nucleophilic 1,2-addition o...
Asymmetric synthesis of a-(heteroaryl)alkylamines and a -amino acids via nucleophilic 1,2-addition of lithiated heterocycles to aldehyde SAMP-hydrazones
Authors : Dieter Enders, Giuseppe Del Signore, Gerhard Raabe
Pages : 492-518
Doi:10.3906/kim-1302-71
View : 12 | Download : 5
Publication Date : 9999-12-31
Article Type : Makaleler
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%).Keywords : Amines, asymmetric synthesis, SAMP-hydrazone, nucleophilic addition, amino acids