Enantioselective Iridium-Catalyzed Hydrogenation of α-Keto Amides to α-Hydroxy Amides
| Autor: | Xumu Zhang, Hua Qian, Jiang Wang, Jialin Wen, Li Dang, Ouran Yu, Tilong Yang, Guoxian Gu |
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| Rok vydání: | 2017 |
| Předmět: |
Reaction mechanism
010405 organic chemistry Chemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis Organic chemistry Density functional theory Iridium Physical and Theoretical Chemistry Enantiomer |
| Zdroj: | Organic Letters. 19:5920-5923 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b02912 |
| Popis: | A highly enantioselective iridium-catalyzed hydrogenation of α-keto amides to form α-hydroxy amides has been achieved with excellent results (up to >99% conversion and up to >99% ee, TON up to 100 000). As an example, this protocol was applied to the synthesis of (S)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol, the enantiomer of norepinephrine, which is widely used as an injectable drug for the treatment of critically low blood pressure. Density functional theory (DFT) calculations were also carried out to reveal the reaction mechanism. |
| Databáze: | OpenAIRE |
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