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High Throughput Scr...
High Throughput Screening of a Catalyst Library for the Asymmetric Transfer Hydrogenation of Heteroaromatic Ketones : Formal Syntheses of (R)-Fluoxetine and (S)-Duloxetine
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- Buitrago, Elina (author)
- Stockholms universitet,Institutionen för organisk kemi
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- Lundberg, Helena (author)
- Stockholms universitet,Institutionen för organisk kemi
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- Andersson, Hans (author)
- Stockholms universitet,Institutionen för organisk kemi
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Ryberg, Per (author)
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- Adolfsson, Hans (author)
- Stockholms universitet,Institutionen för organisk kemi
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(creator_code:org_t)
- 2012-09-07
- 2012
- English.
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In: ChemCatChem. - : Wiley. - 1867-3880 .- 1867-3899. ; 4:12, s. 2082-2089
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- A total of 21 amino acid based ligands including hydroxy amide, thioamide, and hydroxamic acid functionalities, respectively, were combined with [Ru(p-cymene)Cl2]2 and [RhCp*Cl2]2, and used as catalysts for the asymmetric transfer hydrogenation of four different heteroaromatic ketones in 2-propanol. The reactions were performed on a Chemspeed automated high-throughput screening robotic platform. Optimal catalysts were identified for the individual heterocyclic substrate classes. Based on these results, the formal syntheses of the antidepressant drugs (R)-fluoxetine and (S)-duloxetine were conducted by using the found catalysts in the key reaction step, which results in high isolated yields (94?%) and excellent product enantioselectivities (>99?% ee) of the formed 1,3-amino alcohols.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- amino acids
- asymmetric synthesis
- enantioselectivity
- hydrogenation
- transition metals
Publication and Content Type
- ref (subject category)
- art (subject category)
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