REGIOSELECTIVE CONTROL IN THE REACTIONS ALPHA-AMINOALKYLCUPRATES WITHALLYLIC SUBSTRATES

Authors
DIETER RK VELU SE NICE LE
Citation
Rk. Dieter et al., REGIOSELECTIVE CONTROL IN THE REACTIONS ALPHA-AMINOALKYLCUPRATES WITHALLYLIC SUBSTRATES, Synlett, (9), 1997, pp. 1114-1116
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
9
Year of publication
1997
Pages
1114 - 1116
Database
ISI
SICI code
0936-5214(1997):9<1114:RCITRA>2.0.ZU;2-2
Abstract
Organocuprate reagents prepared from alpha-aminoalkyllithium reagents and CuCN react with allylic electrophiles to afford homoallylic amines . Allylic sulfides of benzothiazole-2-thiol give exclusively substitut ion products without rearrangement while cuprate reagents prepared fro m primary alpha-aminoalkyl ligands react with allylic bromides to give rearranged substitution products with modest regioselectivity. Chemic al yields and regioselectivities are dependent upon solvent, substrate leaving group, added LiCl salt, and alpha-aminoalkyl ligand.