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• W2040803702 abstract "A series of chiral organophosphine oxide/sulfide-substituted binaphtholate ligands have been prepared ({(R)-H2BINOL-[P(O)R2]2}2-, R = Ph, Et, tBu, 3,5-xylyl, Bn, and OEt; {(R)-H2BINOL-[P(S)Ph2]2}2-). The X-ray crystal structures of (R)-H2BINOL-[P(O)R2]2 (R = Ph, Et, and tBu) evidence the varying binaphtholate dihedral angles and conformational flexibility possible for these ligands. Precatalysts for enantioselective intramolecular aminoalkene hydroamination/cyclization are conveniently generated in situ from the metal homoleptic dialkylamido precursors Ln[N(SiMe3)2]3 (Ln = La, Nd, Sm, Y, Lu, and Sc) and the above binaphthols. The crystal structure of La2{(R)-BINOL-[P(O)Ph2]2}3 reveals strong coordination of lanthanide ion by the phosphine oxide moieties. Enantioselectivities as high as 65% ee for the hydroamination/cyclization of 2,2-dimethylpent-4-enylamine are obtained with {(R)-BINOL-[P(O)Et2]2}NdN(SiMe3)2 at room temperature. Lanthanide catalysts having varying organophosphine oxide-substituted binaphtholate ligands exhibit differing enantioselectivity trends with decreasing Ln3+ ionic radius, whereas Sc3+ catalysts afford enantioselectivities with opposite product configurations. Kinetic studies reveal that the hydroamination rate is zero-order in [aminoalkene], consistent with the generally accepted mechanism for organolanthanide-catalyzed hydroamination/cyclization." @default.
• W2040803702 created "2016-06-24" @default.
• W2040803702 creator A5000731301 @default.
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• W2040803702 date "2006-12-14" @default.
• W2040803702 modified "2023-09-27" @default.
• W2040803702 title "Organophosphine Oxide/Sulfide-Substituted Lanthanide Binaphtholate Catalysts for Enantioselective Hydroamination/Cyclization" @default.
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• W2040803702 doi "https://doi.org/10.1021/om0607999" @default.
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