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Second-Generation Amino Acid Furanoside Based Ligands from D-Glucose for the Asymmetric Transfer Hydrogenation of Ketones
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2013 (English)In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 5, no 12, 3821-3828 p.Article in journal (Refereed) Published
Abstract [en]

A novel series of modular amino acid thioamide ligands functionalized with carbohydrates were introduced and employed in the rhodium-catalyzed asymmetric transfer hydrogenation (ATH) of aryl alkyl ketones, including the less-studied heteroaromatic ketones. The ligands are based on amino acid hydroxyamides (pseudodipeptides), which are the most successful ligands previously used in asymmetric hydrogen transfer reactions. High enantioselectivities [up to 99% enantiomeric excess (ee)] were achieved in the ATH of a wide range of aryl alkyl ketones by using catalysts generated insitu from [RhCl2Cp*](2) (Cp*=C5Me5) and thioamide ligands comprising a 3-benzyl glucofuranoside backbone and a bulky isopropyl group in the -amino acid moiety. Interestingly, both enantiomers of the alcohol products can readily be obtained with high enantioselectivity by simply changing the absolute configuration of the -amino acid. The good performance can be extended to a very challenging class of industrially interesting heteroaromatic ketones (up to 99%ee).

Place, publisher, year, edition, pages
2013. Vol. 5, no 12, 3821-3828 p.
Keyword [en]
asymmetric synthesis, glycosides, hydrogen transfer, rhodium, thioamides
National Category
Physical Chemistry
Identifiers
URN: urn:nbn:se:su:diva-99136DOI: 10.1002/cctc.201300456ISI: 000327424500052OAI: oai:DiVA.org:su-99136DiVA: diva2:686699
Funder
Swedish Research CouncilKnut and Alice Wallenberg Foundation
Note

AuthorCount:4;

Available from: 2014-01-13 Created: 2014-01-12 Last updated: 2017-12-06Bibliographically approved

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