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Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines

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Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines. / Gilbert, Sophie H.; Tin, Sergey; Fuentes, José A.; Fanjul, Tamara; Clarke, Matthew L.

In: Tetrahedron, Vol. In Press, 131863, 10.12.2020.

Research output: Contribution to journalArticlepeer-review

Harvard

Gilbert, SH, Tin, S, Fuentes, JA, Fanjul, T & Clarke, ML 2020, 'Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines', Tetrahedron, vol. In Press, 131863. https://doi.org/10.1016/j.tet.2020.131863

APA

Gilbert, S. H., Tin, S., Fuentes, J. A., Fanjul, T., & Clarke, M. L. (2020). Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines. Tetrahedron, In Press, [131863]. https://doi.org/10.1016/j.tet.2020.131863

Vancouver

Gilbert SH, Tin S, Fuentes JA, Fanjul T, Clarke ML. Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines. Tetrahedron. 2020 Dec 10;In Press. 131863. https://doi.org/10.1016/j.tet.2020.131863

Author

Gilbert, Sophie H. ; Tin, Sergey ; Fuentes, José A. ; Fanjul, Tamara ; Clarke, Matthew L. / Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines. In: Tetrahedron. 2020 ; Vol. In Press.

Bibtex - Download

@article{00adc5db81954b51a13bbaae19ade6b5,
title = "Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines",
abstract = "An asymmetric hydrogenation of enamines is efficiently catalysed by rhodium complexed with a fluorinated version of the planar chiral paracyclophane-diphosphine ligand, Phanephos. This catalyst was shown to be very active, with examples operating at just 0.1 mol% of catalyst. This catalyst was then successfully adapted to Direct Asymmetric Reductive Amination, leading to the formation of several tertiary amines with moderate e.e., if activated ketone/amine partners are used.",
keywords = "Enamine hydrogenation, Electronic effects, Enantioselective hydrogenation, Planar chirality, Deuterium labelling",
author = "Gilbert, {Sophie H.} and Sergey Tin and Fuentes, {Jos{\'e} A.} and Tamara Fanjul and Clarke, {Matthew L.}",
note = "We would like to thank the University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [Ph.D. studentship to SHG (PhD 2019); Grant code: EP/L016419/1], and Dr Reddys (EU Ltd.) for co-supporting a University studentship to ST (PhD 2017).",
year = "2020",
month = dec,
day = "10",
doi = "10.1016/j.tet.2020.131863",
language = "English",
volume = "In Press",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines

AU - Gilbert, Sophie H.

AU - Tin, Sergey

AU - Fuentes, José A.

AU - Fanjul, Tamara

AU - Clarke, Matthew L.

N1 - We would like to thank the University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [Ph.D. studentship to SHG (PhD 2019); Grant code: EP/L016419/1], and Dr Reddys (EU Ltd.) for co-supporting a University studentship to ST (PhD 2017).

PY - 2020/12/10

Y1 - 2020/12/10

N2 - An asymmetric hydrogenation of enamines is efficiently catalysed by rhodium complexed with a fluorinated version of the planar chiral paracyclophane-diphosphine ligand, Phanephos. This catalyst was shown to be very active, with examples operating at just 0.1 mol% of catalyst. This catalyst was then successfully adapted to Direct Asymmetric Reductive Amination, leading to the formation of several tertiary amines with moderate e.e., if activated ketone/amine partners are used.

AB - An asymmetric hydrogenation of enamines is efficiently catalysed by rhodium complexed with a fluorinated version of the planar chiral paracyclophane-diphosphine ligand, Phanephos. This catalyst was shown to be very active, with examples operating at just 0.1 mol% of catalyst. This catalyst was then successfully adapted to Direct Asymmetric Reductive Amination, leading to the formation of several tertiary amines with moderate e.e., if activated ketone/amine partners are used.

KW - Enamine hydrogenation

KW - Electronic effects

KW - Enantioselective hydrogenation

KW - Planar chirality

KW - Deuterium labelling

UR - https://www.sciencedirect.com/science/article/pii/S0040402020311212?via=ihub#appsec1

U2 - 10.1016/j.tet.2020.131863

DO - 10.1016/j.tet.2020.131863

M3 - Article

VL - In Press

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

M1 - 131863

ER -

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