Asymmetric reduction of ketones with ruthenium-oxazoline based catalysts

Debono, Nathalie; Pinel, Catherine; Jahjah, Rabih; Alaaeddine, Ali; Delichère, P.; Lefèbvre, Frédéric; Djakovitch, Laurent

doi:10.1016/j.molcata.2008.03.012

Cited by 5 publications

(1 citation statement)

References 24 publications

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“…At the outset of studies to render the reaction enantioselective, it was important to recognize that allylruthenium agents typically react with carbonyl compounds through a 6-membered transition state . This feature presents the opportunity to apply methods that have been successfully employed in other related reactions to induce stereoselection. − Two viable strategies presented themselves: (1) the inclusion of an chiral ion that will associate with the ruthenium metal and direct the approach of the incoming aldehyde or (2) the formation of a discrete ligated ruthenium complex that will prefer a particular 6-membered transition state leading to enantioenriched products. − …”

Section: Resultsmentioning

confidence: 99%

Catalytic Nucleophilic Allylation Driven by the Water–Gas Shift Reaction

et al. 2017

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The ruthenium-catalyzed allylation of aldehydes with allylic pro-nucleophiles has been demonstrated to be an efficient means to form carbon–carbon bonds under mild conditions. The evolution of this reaction from the initial serendipitous discovery to its general synthetic scope is detailed, highlighting the roles of water, CO, and amine in the generation of a more complete catalytic cycle. The use of unsymmetrical allylic pro-nucleophiles was shown to give preferential product formation through the modulation of reaction conditions. Both (E)-cinnamyl acetate and vinyl oxirane were efficiently used to form the anti-branched products (up to >20:1 anti/syn) and E-linear products (up to >20:1 E/Z) in high selectivity with aromatic, α,β-unsaturated, and aliphatic aldehydes, respectively. Attempts to render the reaction enantioselective are highlighted and include enantioenrichment of up to 75:25 for benzaldehyde.

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Section: Resultsmentioning

confidence: 99%

Catalytic Nucleophilic Allylation Driven by the Water–Gas Shift Reaction

et al. 2017

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BOX Structures with Additional Coordination Sites: Potential Ligands for Bifunctional Catalysis

Seifermann¹,

Müller²,

Bräse³

2013

Eur J Org Chem

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The synthesis of four new bis(oxazoline) (BOX) derivatives bearing two additional coordination sites at the 4,4′‐positions is presented. As these BOX scaffolds contain an unsubstituted methylene bridge, they should be capable of forming neutral metal complexes. Thus, these molecules are very interesting ligands for bifunctional catalysis. In addition, one BOX scaffold bearing two azide moieties was successfully employed in copper‐free 1,3‐dipolar cycloaddition reactions. The resulting products have yet again high ligand potential.

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