General asymmetric hydrogenation of 2-alkyl- and 2-aryl-substituted quinoxaline derivatives catalyzed by iridium-difluorphos: Unusual halide effect and synthetic application

Damien Cartigny, Farouk Berhal, Takuto Nagano, Phannarath Phansavath, Tahar Ayad, Jean Pierre Genêt, Takashi Ohshima, Kazushi Mashima, Virginie Ratovelomanana-Vidal

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42 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)4544-4556
Number of pages13
JournalJournal of Organic Chemistry
Volume77
Issue number10
DOIs
Publication statusPublished - May 18 2012

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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