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Enantioselective Catalysis. 157 [1] Carbohydrate‐Based, Water‐Soluble Ligands for the Stereoselective Hydrogenation of Folic Acid
Author(s) -
Brunner Henri,
Keck Christian
Publication year - 2005
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200500037
Subject(s) - chemistry , stereoselectivity , catalysis , enantioselective synthesis , hydrolysis , oxime , organic chemistry , folic acid , combinatorial chemistry , acetylation , ether , biochemistry , medicine , gene
The new chiral ligands 11 – 30 were synthesized by combining aldehydes and ketones, able for coordination, with mono‐ and disaccharides via oxime ether bridges stable towards hydrolysis. Due to their OH groups they were water‐soluble (except 11 and 19 ), whereas their acetylated analogs dissolved in organic solvents. The new ligands were used in homogeneous and heterogenized catalysts for the stereoselective hydrogenation of folic acid 31 , the formylated hydrogenation product 33 of which is the anticancer drug Leucovorine.