Title of article
Asymmetric synthesis of alpha-(heteroaryl)alkylamines and alpha -amino acids via nucleophilic 1,2-addition of lithiated heterocycles to aldehyde SAMP-hydrazones
Author/Authors
ENDERS, Dieter RWTH Aachen University - Institut für Organische Chemie, Germany , DEL SIGNORE, Giuseppe RWTH Aachen University - Institute of Organic Chemistry, Germany , DEL SIGNORE, Giuseppe Mercachem BV, the Netherlands , RAABE, Gerhard RWTH Aachen University - Institute of Organic Chemistry, Germany
From page
492
To page
518
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
Journal title
Turkish Journal of Chemistry
Journal title
Turkish Journal of Chemistry
Record number
2533276
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