Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity

Ahmed F. Abdel-Magied; Yusuf Theibich; Amrendra K. Singh; Ahibur Rahaman; Isa Doverbratt; Arun K. Raha; Matti Haukka; Michael G. Richmond; Ebbe Nordlander

doi:10.1039/c9dt04799a

Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity

Ahmed F. Abdel-Magied, Yusuf Theibich, Amrendra K. Singh, Ahibur Rahaman, Isa Doverbratt, Arun K. Raha, Matti Haukka, Michael G. Richmond, Ebbe Nordlander

Research output: Contribution to journal › Article › peer-review

Abstract

Twenty clusters of the general formula [(μ-H)₂Ru₃(μ₃-S)(CO)₇(μ-P-P∗)] (P-P∗ = chiral diphosphine of the ferrocene-based Walphos or Josiphos families) have been synthesised and characterised. The clusters have been tested as catalysts for asymmetric hydrogenation of tiglic acid [trans-2-methyl-2-butenoic acid]. The observed enantioselectivities and conversion rates strongly support catalysis by intact Ru₃ clusters. A catalytic mechanism involving an active Ru₃ catalyst generated by CO loss from [(μ-H)₂Ru₃(μ₃-S)(CO)₇(μ-P-P∗)] has been investigated by DFT calculations.

Original language	English
Pages (from-to)	4244-4256
Number of pages	13
Journal	Dalton Transactions
Volume	49
Issue number	14
DOIs	https://doi.org/10.1039/c9dt04799a
Publication status	Published - 2020

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Physical Chemistry (including Surface- and Colloid Chemistry)

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Abdel-Magied, A. F., Theibich, Y., Singh, A. K., Rahaman, A., Doverbratt, I., Raha, A. K., Haukka, M., Richmond, M. G., & Nordlander, E. (2020). Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity. Dalton Transactions, 49(14), 4244-4256. https://doi.org/10.1039/c9dt04799a

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title = "Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity",

abstract = "Twenty clusters of the general formula [(μ-H)2Ru3(μ3-S)(CO)7(μ-P-P∗)] (P-P∗ = chiral diphosphine of the ferrocene-based Walphos or Josiphos families) have been synthesised and characterised. The clusters have been tested as catalysts for asymmetric hydrogenation of tiglic acid [trans-2-methyl-2-butenoic acid]. The observed enantioselectivities and conversion rates strongly support catalysis by intact Ru3 clusters. A catalytic mechanism involving an active Ru3 catalyst generated by CO loss from [(μ-H)2Ru3(μ3-S)(CO)7(μ-P-P∗)] has been investigated by DFT calculations.",

author = "Abdel-Magied, \{Ahmed F.\} and Yusuf Theibich and Singh, \{Amrendra K.\} and Ahibur Rahaman and Isa Doverbratt and Raha, \{Arun K.\} and Matti Haukka and Richmond, \{Michael G.\} and Ebbe Nordlander",

year = "2020",

doi = "10.1039/c9dt04799a",

language = "English",

volume = "49",

pages = "4244--4256",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "14",

}

Abdel-Magied, AF, Theibich, Y, Singh, AK, Rahaman, A, Doverbratt, I, Raha, AK, Haukka, M, Richmond, MG & Nordlander, E 2020, 'Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity', Dalton Transactions, vol. 49, no. 14, pp. 4244-4256. https://doi.org/10.1039/c9dt04799a

TY - JOUR

T1 - Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity

AU - Abdel-Magied, Ahmed F.

AU - Theibich, Yusuf

AU - Singh, Amrendra K.

AU - Rahaman, Ahibur

AU - Doverbratt, Isa

AU - Raha, Arun K.

AU - Haukka, Matti

AU - Richmond, Michael G.

AU - Nordlander, Ebbe

PY - 2020

Y1 - 2020

N2 - Twenty clusters of the general formula [(μ-H)2Ru3(μ3-S)(CO)7(μ-P-P∗)] (P-P∗ = chiral diphosphine of the ferrocene-based Walphos or Josiphos families) have been synthesised and characterised. The clusters have been tested as catalysts for asymmetric hydrogenation of tiglic acid [trans-2-methyl-2-butenoic acid]. The observed enantioselectivities and conversion rates strongly support catalysis by intact Ru3 clusters. A catalytic mechanism involving an active Ru3 catalyst generated by CO loss from [(μ-H)2Ru3(μ3-S)(CO)7(μ-P-P∗)] has been investigated by DFT calculations.

AB - Twenty clusters of the general formula [(μ-H)2Ru3(μ3-S)(CO)7(μ-P-P∗)] (P-P∗ = chiral diphosphine of the ferrocene-based Walphos or Josiphos families) have been synthesised and characterised. The clusters have been tested as catalysts for asymmetric hydrogenation of tiglic acid [trans-2-methyl-2-butenoic acid]. The observed enantioselectivities and conversion rates strongly support catalysis by intact Ru3 clusters. A catalytic mechanism involving an active Ru3 catalyst generated by CO loss from [(μ-H)2Ru3(μ3-S)(CO)7(μ-P-P∗)] has been investigated by DFT calculations.

UR - https://www.scopus.com/pages/publications/85083042566

U2 - 10.1039/c9dt04799a

DO - 10.1039/c9dt04799a

M3 - Article

C2 - 32103214

AN - SCOPUS:85083042566

SN - 1477-9226

VL - 49

SP - 4244

EP - 4256

JO - Dalton Transactions

JF - Dalton Transactions

IS - 14

ER -

Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity

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