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DOI: 10.1055/s-0028-1083613
Amino Acid Derived Sulfinamide Ligands for Transfer Hydrogenation
Contributor(s):Hisashi Yamamoto, Joshua N. PayetteStockholm University, Sweden
Synthesis of Novel Amino-Acid-Derived Sulfinamides and Their Evaluation as Ligands for the Enantioselective Transfer Hydrogenation of Ketones
Eur. J. Org. Chem. 2008, 4655-4664
Publication History
Publication Date:
20 November 2008 (online)
Key words
sulfinamides - ruthenium - transfer hydrogenation
Significance
While chiral sulfoxides have found numerous applications as chiral ligands in various asymmetric transformations, few reports of related chiral sulfinamides as ligands exist. Here, the authors describe the design and synthesis of several chiral sulfinamides from simple amino acids. With ruthenium as metal source, these ligands were applied in the asymmetric transfer hydrogenation of several acetophenone derivatives to give products in modest yields and with high ee values.
Comment
The authors have described the design and application of a novel and easily accessible class of chiral sulfinamide ligands. Control experiments with ligands where the sulfinamide moiety was replaced with a nonchiral sulfonamide unit gave corresponding benzyl alcohols in modest yields but low ee values (<5%). Thus, the authors postulate that the chiral sulfinamide group is crucial for enantiofacial discrimination. Further applications of this interesting and novel class of ligands are anticipated.