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

Authors :
Cartigny D
Berhal F
Nagano T
Phansavath P
Ayad T
GenĂȘt JP
Ohshima T
Mashima K
Ratovelomanana-Vidal V
Source :
The Journal of organic chemistry [J Org Chem] 2012 May 18; Vol. 77 (10), pp. 4544-56. Date of Electronic Publication: 2012 Apr 30.
Publication Year :
2012

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).

Details

Language :
English
ISSN :
1520-6904
Volume :
77
Issue :
10
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
22519599
Full Text :
https://doi.org/10.1021/jo300455y