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Catalytic Asymmetric Hydrogenation of Pyrimidines
Author(s) -
Kuwano Ryoichi,
Hashiguchi Yuta,
Ikeda Ryuhei,
Ishizuka Kentaro
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410607
Subject(s) - iridium , catalysis , chemistry , trifluoromethanesulfonate , asymmetric hydrogenation , cyclooctadiene , ferrocene , enantioselective synthesis , substrate (aquarium) , yield (engineering) , lanthanide , ligand (biochemistry) , chiral ligand , organic chemistry , combinatorial chemistry , medicinal chemistry , materials science , ion , electrochemistry , biochemistry , oceanography , receptor , electrode , geology , metallurgy
The asymmetric hydrogenation of pyrimidines proceeded with high enantioselectivity (up to 99 % ee ) using an iridium catalyst composed of [IrCl(cod)] 2 , a ferrocene‐containing chiral diphosphine ligand (Josiphos), iodine, and Yb(OTf) 3 (cod=1,5‐cyclooctadiene). The chiral catalyst converted various 4‐substituted pyrimidines into chiral 1,4,5,6‐tetrahydropyrimidines in high yield. The lanthanide triflate is crucial for achieving the high enantioselectivity as well as for activating the heteroarene substrate.