Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 10, Pages 4544-4556Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300455y
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Funding
- CNRS
- French Ministere de l'Education et de la Recherche
- JSPS-CNRS
- Grants-in-Aid for Scientific Research [22105010, 24106733] Funding Source: KAKEN
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A general asymmetric hydrogenation of a wide range of 2-alkyl- and 2-aryl-substituted quinoxaline derivatives catalyzed by an iridium-difluorphos complex has been developed. Under mild reaction conditions, the corresponding biologically relevant 2-substituted-1,2,3,4-tetrahydroquinoxaline units were obtained in high yields and good to excellent enantioselectivities up to 95%. With a catalyst ratio of S/C = 1000 and on a gram scale, the catalytic activity of the Ir-difluorphos complex was maintained showing its potential value. Finally, we demonstrated the application of our process in the synthesis of compound (S)-9, which is an inhibitor of cholesteryl ester transfer protein (CETP).
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