Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 10, Pages 2293-2302Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201301112
Keywords
asymmetric catalysis; carbohydrates; ketones; rhodium; ruthenium; transfer hydrogenation
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Funding
- Spanish Government [CTQ2010-15835]
- Catalan Government [2009SGR116]
- ICREA Foundation through ICREA Academia awards
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A large library of pyranoside-based hydroxyamide and thioamide ligands has been synthesized for asymmetric transfer hydrogenation in an attempt to expand the scope of the substrates to cover a broader range of challenging heteroaromatic and aryl/fluoroalkyl ketones. These ligands have the advantage that they are prepared from commercial D-glucose, D-glucosamine and a-amino acids, inexpensive natural chiral feedstocks. By carefully selecting the ligand components (substituents/configurations at the amide/thioamide moiety, the position of amide/thioamide group and the configuration at C-2), we found that pyranoside-based thioamide ligands provided excellent enantioselectivities (in the best cases, ees of >99% were achieved) in a broad range of ketones, including the less studied heteroaromatics and challenging aryl/fluoroalkyls. Note that both enantiomers of the reduction products can be obtained with excellent enantioselectivities by simply changing the absolute configuration of the thioamide substituent.
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