The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature. Quality Control of (1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol, 136030-00-7, Name is (1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol, SMILES is O[C@@H]1[C@H](N)C2=C(C=CC=C2)C1, in an article , author is Nagae, Haruki, once mentioned of 136030-00-7.
Asymmetric Allylic Alkylation of beta-Ketoesters via C-N Bond Cleavage of N-Allyl-N-methylaniline Derivatives Catalyzed by a Nickel-Diphosphine System
Nickel complexes bearing chiral diphosphine ligands, such as (S)-Tol-MeO-BIPHEP and (S)-H-8-BINAP, serve as efficient catalysts for asymmetric allylic alkylation (AAA) of beta-ketoesters, using allylic amines as ally! 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 beta-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 beta-ketoester is key to cleaving the C-N bond and delivering a cationic pi-allyl nickel(II) intermediate.
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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
,Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis