Asymmetric Transfer Hydrogenations of 2,3-Disubstituted Quinoxalines with Ammonia Borane
| Autor: | Haifeng Du, Wei Meng, Songlei Li |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Hydrogen
010405 organic chemistry Chemistry Organic Chemistry Ammonia borane chemistry.chemical_element Borane 010402 general chemistry Transfer hydrogenation 01 natural sciences Biochemistry Frustrated Lewis pair 0104 chemical sciences Catalysis chemistry.chemical_compound Organic chemistry Physical and Theoretical Chemistry Cis–trans isomerism |
| Zdroj: | Organic letters. 19(10) |
| ISSN: | 1523-7052 |
| Popis: | An asymmetric transfer hydrogenation of 2,3-disubstituted quinoxalines using a chiral frustrated Lewis pair of Piers’ borane and (R)-tert-butylsulfinamide as the catalyst with ammonia borane as the hydrogen source has been successfully realized. For 2-alkyl-3-arylquinoxaline substrates, cis-tetrahydroquinoxalines were obtained as the predominant products in high yields with 77–86% ee. In contrast, trans isomers were often furnished as major products for the reactions of 2,3-dialkylquinoxalines with up to >99% ee. |
| Databáze: | OpenAIRE |
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