99679-79-5Relevant academic research and scientific papers
Modular hydroxyamide and thioamide pyranoside-based ligand library from the sugar pool: New class of ligands for asymmetric transfer hydrogenation of ketones
Coll, Mercè,Pàmies, Oscar,Diéguez, Montserrat
supporting information, p. 2293 - 2302 (2014/07/21)
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 α-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.
Enolates of Carbohydrates, 4. - Axial C-Alkylation in α-Position of α-Amino-α-deoxy-ketoses
Klemer, Almuth,Wilbers, Hubert
, p. 2328 - 2341 (2007/10/02)
Products of type 2a-c, 6, 10a, b, and 14a, b which are alkylated in α-position of the keto function are yielded by reaction of the α-amino-α-deoxy-uloses 1a-c, 5, 9a, and 13a, b with LDA, CH3I, HMPA in THF (method A) or KOtBu, CH3I in DMF (method B) in a
