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

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Abstract

Twenty clusters of the general formula [(μ-H)2Ru33-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)2Ru33-S)(CO)7(μ-P–P*)] has been investigated by DFT calculations.

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

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Article information


Submitted
17 Dec 2019
Accepted
14 Feb 2020
First published
27 Feb 2020

Dalton Trans., 2020, Advance Article
Article type
Paper

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

A. F. Abdel-Magied, Y. Theibich, A. K. Singh, A. Rahaman, I. Doverbratt, A. K. Raha, M. Haukka, M. G. Richmond and E. Nordlander, Dalton Trans., 2020, Advance Article , DOI: 10.1039/C9DT04799A

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