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  The preparation of ferrocene-containing phosphinamine ligands possessing central and planar chirality and their application in palladium-catalysed allylic substitution

Meaney, K., Goddard, R., Bronger, R. P. J., & Guiry, P. J. (2021). The preparation of ferrocene-containing phosphinamine ligands possessing central and planar chirality and their application in palladium-catalysed allylic substitution. Tetrahedron, 90: 132088. doi:10.1016/j.tet.2021.132088.

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 Creators:
Meaney, Keith1, Author
Goddard, Richard2, Author           
Bronger, Raymond P. J.1, Author
Guiry, Patrick J.1, Author
Affiliations:
1Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland, ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: Ferrocene ligands; Chiral PN Ligands; Pd-catalysed asymmetric allylic alkylation; Mechanistic studies
 Abstract: The preparation of four novel ferrocenylphosphinamine ligands, possessing both planar and central chirality, is described. The absolute configuration of two of the ligands was confirmed by X-ray crystallographic analysis. The palladium complexes of these new ligands were applied in the allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate to study the effect of planar chirality and/or the trimethylsilyl group. Quantitative yields with ees of up to 77% were obtained with the ligand that bears both (R)-planar and (R)-central chirality. Application of its trimethylsilyl analogue gave significantly lower ees, whereas the presence of the trimethylsilyl group in the ligand that bears (S)-planar and (R)-central chirality had a beneficial effect on enantioselectivity. Solution 1H NMR spectroscopic studies of the 1,3-diphenylallyl palladium complexes of two of the ligands revealed the major diastereomer in solution does not give rise to the major product observed in allylic alkylation, assuming nucleophilic attack trans to phosphorus.

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Language(s): eng - English
 Dates: 2021-03-102020-12-242021-03-112021-04-032021-06-18
 Publication Status: Published in print
 Pages: 13
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/j.tet.2021.132088
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron : the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry
Source Genre: Journal
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Publ. Info: Kidlington : Elsevier Science
Pages: - Volume / Issue: 90 Sequence Number: 132088 Start / End Page: - Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/00404020