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Imidate-phosphanes as highly versatile N,P ligands and their application in palladium-catalyzed asymmetric allylic alkylation reactions

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Abstract
Chiral imidate-phosphanes were developed as a new type of N,P ligands. These ligands are easily accessible through a one-step procedure starting from a commercially available chiral aminophosphane and an imidate precursor. Excellent performance of the catalyst system was observed with various carbon nucleophiles in the Pd(0)-catalyzed asymmetric allylic alkylation (up to 99% yield and >99 % ee). Moreover, good to excellent enantioselectivities could also be obtained in the allylic alkylation of more difficult linear unhindered substrates and cyclic substrates, demonstrating that this new catalyst system has a broad substrate scope.
Keywords
Palladium, P ligands, N, Asymmetric catalysis, CHIRAL FERROCENYL PHOSPHINES, Imidate ligands, Allylic alkylation, SUBSTITUTION-REACTIONS, OXAZOLINE LIGANDS, INDUCTION, COMPLEXES, ACID

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Chicago
Noël, Timothy, Katrien Bert, Erik Van der Eycken, and Johan Van der Eycken. 2010. “Imidate-phosphanes as Highly Versatile N,P Ligands and Their Application in Palladium-catalyzed Asymmetric Allylic Alkylation Reactions.” European Journal of Organic Chemistry (21): 4056–4061.
APA
Noël, T., Bert, K., Van der Eycken, E., & Van der Eycken, J. (2010). Imidate-phosphanes as highly versatile N,P ligands and their application in palladium-catalyzed asymmetric allylic alkylation reactions. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (21), 4056–4061.
Vancouver
1.
Noël T, Bert K, Van der Eycken E, Van der Eycken J. Imidate-phosphanes as highly versatile N,P ligands and their application in palladium-catalyzed asymmetric allylic alkylation reactions. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2010;(21):4056–61.
MLA
Noël, Timothy, Katrien Bert, Erik Van der Eycken, et al. “Imidate-phosphanes as Highly Versatile N,P Ligands and Their Application in Palladium-catalyzed Asymmetric Allylic Alkylation Reactions.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 21 (2010): 4056–4061. Print.
@article{1980287,
  abstract     = {Chiral imidate-phosphanes were developed as a new type of N,P ligands. These ligands are easily accessible through a one-step procedure starting from a commercially available chiral aminophosphane and an imidate precursor. Excellent performance of the catalyst system was observed with various carbon nucleophiles in the Pd(0)-catalyzed asymmetric allylic alkylation (up to 99\% yield and {\textrangle}99 \% ee). Moreover, good to excellent enantioselectivities could also be obtained in the allylic alkylation of more difficult linear unhindered substrates and cyclic substrates, demonstrating that this new catalyst system has a broad substrate scope.},
  author       = {No{\"e}l, Timothy and Bert, Katrien and Van der Eycken, Erik and Van der Eycken, Johan},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {Palladium,P ligands,N,Asymmetric catalysis,CHIRAL FERROCENYL PHOSPHINES,Imidate ligands,Allylic alkylation,SUBSTITUTION-REACTIONS,OXAZOLINE LIGANDS,INDUCTION,COMPLEXES,ACID},
  language     = {eng},
  number       = {21},
  pages        = {4056--4061},
  title        = {Imidate-phosphanes as highly versatile N,P ligands and their application in palladium-catalyzed asymmetric allylic alkylation reactions},
  url          = {http://dx.doi.org/10.1002/ejoc.201000238},
  year         = {2010},
}

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