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Turkish Journal of Chemistry

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\%).

First Page

492

Last Page

518

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