A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren

Jeroen A.F. Boogers; Ulfried Felfer; Martina Kotthaus; Laurent Lefort; Gerhard Steinbauer; André H.M. de Vries; Johannes G. de Vries

doi:10.1021/op0602369

Publication

A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren

Boogers, J. A. F., Felfer, U., Kotthaus, M., Lefort, L., Steinbauer, G., Vries, A. H. M. D. & Vries, J. G. D., 2007, In : Organic Process Research & Development. 11, 3, 7 p.

Research output: Contribution to journal › Article › Academic

APA

Boogers, J. A. F., Felfer, U., Kotthaus, M., Lefort, L., Steinbauer, G., Vries, A. H. M. D., & Vries, J. G. D. (2007). A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren. Organic Process Research & Development, 11(3). https://doi.org/10.1021/op0602369

Author

Boogers, Jeroen A.F. ; Felfer, Ulfried ; Kotthaus, Martina ; Lefort, Laurent ; Steinbauer, Gerhard ; Vries, André H.M. de ; Vries, Johannes G. de. / A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren. In: Organic Process Research & Development. 2007 ; Vol. 11, No. 3.

Harvard

Boogers, JAF, Felfer, U, Kotthaus, M, Lefort, L, Steinbauer, G, Vries, AHMD & Vries, JGD 2007, 'A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren', Organic Process Research & Development, vol. 11, no. 3. https://doi.org/10.1021/op0602369

Standard

A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren. / Boogers, Jeroen A.F.; Felfer, Ulfried; Kotthaus, Martina; Lefort, Laurent; Steinbauer, Gerhard; Vries, André H.M. de; Vries, Johannes G. de.

In: Organic Process Research & Development, Vol. 11, No. 3, 2007.

Research output: Contribution to journal › Article › Academic

Vancouver

Boogers JAF, Felfer U, Kotthaus M, Lefort L, Steinbauer G, Vries AHMD et al. A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren. Organic Process Research & Development. 2007;11(3). https://doi.org/10.1021/op0602369

BibTeX

@article{a954ec9ab26a4cedb75cc121870fcfe7,

title = "A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren",

abstract = "An asymmetric hydrogenation process for an α-isopropyl dihydrocinnamic acid derivative, an intermediate for the renin inhibitor aliskiren, has been developed using a rhodium catalyst ligated with a chiral monodentate phosphoramidite and a nonchiral phosphine. Whereas catalysts based on two equivalents of monodentate phosphoramidites gave promising results, the rate of hydrogenation and ee of the product could be improved spectacularly by the addition of monodentate nonchiral triarylphosphines to these catalysts. This remarkable mixed-ligand catalyst has been identified using high-throughput experimentation. With the best catalysts turnover numbers >5000 mol mol-1, turnover frequencies >1000 mol mol-1 h-1, and ee{\textquoteright}s up to 95% have been achieved.",

author = "Boogers, {Jeroen A.F.} and Ulfried Felfer and Martina Kotthaus and Laurent Lefort and Gerhard Steinbauer and Vries, {Andr{\'e} H.M. de} and Vries, {Johannes G. de}",

note = "Relation: https://www.rug.nl/scheikunde/ date_submitted:2007 Rights: University of Groningen. Stratingh Institute",

year = "2007",

doi = "10.1021/op0602369",

language = "English",

volume = "11",

journal = "Organic Process Research and Development",

issn = "1083-6160",

publisher = "AMER CHEMICAL SOC INC",

number = "3",

}

RIS

TY - JOUR

T1 - A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren

AU - Boogers, Jeroen A.F.

AU - Felfer, Ulfried

AU - Kotthaus, Martina

AU - Lefort, Laurent

AU - Steinbauer, Gerhard

AU - Vries, André H.M. de

AU - Vries, Johannes G. de

N1 - Relation: https://www.rug.nl/scheikunde/ date_submitted:2007 Rights: University of Groningen. Stratingh Institute

PY - 2007

Y1 - 2007

N2 - An asymmetric hydrogenation process for an α-isopropyl dihydrocinnamic acid derivative, an intermediate for the renin inhibitor aliskiren, has been developed using a rhodium catalyst ligated with a chiral monodentate phosphoramidite and a nonchiral phosphine. Whereas catalysts based on two equivalents of monodentate phosphoramidites gave promising results, the rate of hydrogenation and ee of the product could be improved spectacularly by the addition of monodentate nonchiral triarylphosphines to these catalysts. This remarkable mixed-ligand catalyst has been identified using high-throughput experimentation. With the best catalysts turnover numbers >5000 mol mol-1, turnover frequencies >1000 mol mol-1 h-1, and ee’s up to 95% have been achieved.

AB - An asymmetric hydrogenation process for an α-isopropyl dihydrocinnamic acid derivative, an intermediate for the renin inhibitor aliskiren, has been developed using a rhodium catalyst ligated with a chiral monodentate phosphoramidite and a nonchiral phosphine. Whereas catalysts based on two equivalents of monodentate phosphoramidites gave promising results, the rate of hydrogenation and ee of the product could be improved spectacularly by the addition of monodentate nonchiral triarylphosphines to these catalysts. This remarkable mixed-ligand catalyst has been identified using high-throughput experimentation. With the best catalysts turnover numbers >5000 mol mol-1, turnover frequencies >1000 mol mol-1 h-1, and ee’s up to 95% have been achieved.

U2 - 10.1021/op0602369

DO - 10.1021/op0602369

M3 - Article

VL - 11

JO - Organic Process Research and Development

JF - Organic Process Research and Development

SN - 1083-6160

IS - 3

ER -

ID: 2771273

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