Modular Hydroxyamide and Thioamide Pyranoside‐Based Ligand Library from the Sugar Pool: New Class of Ligands for Asymmetric Transfer Hydrogenation of Ketones. Issue 10 (20th June 2014)

• Record Type: Journal Article
• Authors: Coll, Mercè; Pàmies, Oscar; Diéguez, Montserrat
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 10(2014)
• Page Start: 2293
• Page End: 2302
• Publication Date: 2014-06-20
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201301112
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <sc>D</sc>‐glucose, <sc>D</sc>‐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, <italic>ee</italic>s of &gt;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.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pghnnr45gm" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>