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

Abdel-Magied, Ahmed F. ; Theibich, Yusuf ; Singh, Amrendra K. LU ; Rahaman, Ahibur LU ; Doverbratt, Isa LU ; Raha, Arun K. LU ; Haukka, Matti ; Richmond, Michael G. and Nordlander, Ebbe LU (2020) In Dalton Transactions 49(14). p.4244-4256
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.

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author
; ; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Dalton Transactions
volume
49
issue
14
pages
13 pages
publisher
Royal Society of Chemistry
external identifiers
  • scopus:85083042566
  • pmid:32103214
ISSN
1477-9226
DOI
10.1039/c9dt04799a
language
English
LU publication?
yes
id
8138d627-1595-42c7-bbb1-c46299cfbde4
date added to LUP
2020-04-30 12:25:24
date last changed
2024-05-15 10:24:17
@article{8138d627-1595-42c7-bbb1-c46299cfbde4,
  abstract     = {{<p>Twenty clusters of the general formula [(μ-H)<sub>2</sub>Ru<sub>3</sub>(μ<sub>3</sub>-S)(CO)<sub>7</sub>(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 Ru<sub>3</sub> clusters. A catalytic mechanism involving an active Ru<sub>3</sub> catalyst generated by CO loss from [(μ-H)<sub>2</sub>Ru<sub>3</sub>(μ<sub>3</sub>-S)(CO)<sub>7</sub>(μ-P-P∗)] has been investigated by DFT calculations.</p>}},
  author       = {{Abdel-Magied, Ahmed F. and Theibich, Yusuf and Singh, Amrendra K. and Rahaman, Ahibur and Doverbratt, Isa and Raha, Arun K. and Haukka, Matti and Richmond, Michael G. and Nordlander, Ebbe}},
  issn         = {{1477-9226}},
  language     = {{eng}},
  number       = {{14}},
  pages        = {{4244--4256}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{Dalton Transactions}},
  title        = {{Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity}},
  url          = {{http://dx.doi.org/10.1039/c9dt04799a}},
  doi          = {{10.1039/c9dt04799a}},
  volume       = {{49}},
  year         = {{2020}},
}