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- W3019794126 abstract "Nickel complexes bearing chiral diphosphine ligands, such as (S)-Tol-MeO-BIPHEP and (S)-H8-BINAP, serve as efficient catalysts for asymmetric allylic alkylation (AAA) of β-ketoesters, using allylic amines as allyl sources. The reactions proceed with high catalytic activity and high enantioselectivity. N-Methyl-N-phenyl allylic amines were indispensable to achieve the high catalytic activity, to achieve the high enantioselectivity, and to expand the substrate scope to 5- and 7-membered β-ketoesters, whose nickel-catalyzed AAA with allylic alcohols results in low enantioselectivity. On the basis of the kinetics using a catalyst system made of Ni(cod)2 and (S)-Tol-MeO-BIPHEP, and DFT calculations for the reaction pathway of the AAA reaction mediated by an isolated olefin-coordinated nickel–DPPF complex 4b, we propose a mechanism where protonation of the nitrogen atom of the coordinating allylic amine by β-ketoester is key to cleaving the C–N bond and delivering a cationic π-allyl nickel(II) intermediate." @default.
- W3019794126 created "2020-05-01" @default.
- W3019794126 creator A5001107116 @default.
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- W3019794126 creator A5039400379 @default.
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- W3019794126 creator A5063457576 @default.
- W3019794126 creator A5064611725 @default.
- W3019794126 creator A5072725999 @default.
- W3019794126 date "2020-04-22" @default.
- W3019794126 modified "2023-10-06" @default.
- W3019794126 title "Asymmetric Allylic Alkylation of β-Ketoesters via C–N Bond Cleavage of <i>N</i>-Allyl-<i>N</i>-methylaniline Derivatives Catalyzed by a Nickel–Diphosphine System" @default.
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