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Synlett 1997; 1997(9): 1114-1116
DOI: 10.1055/s-1997-1544
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Regioselective Control in the Reactions of α-Aminoalkylcuprates with Allylic Substrates

R. Karl Dieter* , Sadanandan E. Velu, Lois E. Nice
  • *Hunter Laboratory, Department of Chemistry, Clemson University, Clemson SC 29634-1905, USA
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Publication History

Publication Date:
31 December 2000 (online)

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Organocuprate reagents prepared from α-aminoalkyllithium reagents and CuCN react with allylic electrophiles to afford homoallylic amines. Allylic sulfides of benzothiazole-2-thiol give exclusively substitution products without rearrangement while cuprate reagents prepared from primary α-aminoalkyl ligands react with allylic bromides to give rearranged substitution products with modest regioselectivity. Chemical yields and regioselectivities are dependent upon solvent, substrate leaving group, added LiCl salt, and α-aminoalkyl ligand.

α-aminoalkylcuprates - allylic substitution - copper cyanide - SN2:SN2' ratios - allylic halides - phosphates - sulfides

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