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Full-Text Articles in Physical Sciences and Mathematics
Asymmetric Synthesis Of \Alpha-(Heteroaryl)Alkylamines And \Alpha -Amino Acids Via Nucleophilic 1,2-Addition Of Lithiated Heterocycles To Aldehyde Samp-Hydrazones, Dieter Enders, Giuseppe Del Signore, Gerhard Raabe
Asymmetric Synthesis Of \Alpha-(Heteroaryl)Alkylamines And \Alpha -Amino Acids Via Nucleophilic 1,2-Addition Of Lithiated Heterocycles To Aldehyde Samp-Hydrazones, Dieter Enders, Giuseppe Del Signore, Gerhard Raabe
Turkish Journal of Chemistry
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\%).
Umpolung Strategy: Advances In Catalytic C-C Bond Formations, Serkan Eymur, Mehmet Göllü, Ci̇hangi̇r Tanyeli̇
Umpolung Strategy: Advances In Catalytic C-C Bond Formations, Serkan Eymur, Mehmet Göllü, Ci̇hangi̇r Tanyeli̇
Turkish Journal of Chemistry
This mini-review examines the recent advances in umpolung strategy, devised originally by Corey and Seebach. Although numerous stoichiometric variants have been published to date, this article covers just the catalytic C-C bond forming reactions due to their major benefits such as atom economy, less pollution, and workable simplicity. In the context of umpolung, the studies are evaluated under 3 main titles: enzyme, N-heterocyclic carbene, and cyanide ion catalyzed reactions. In particular, enzyme and NHC catalyzed reactions mainly involve asymmetric applications.