Improved stereoselective synthesis of 3-methoxy- and 3-benzyloxy-16-hydroxymethyl-13α-estra-1,3,5(10)-trien-17-ol isomers by transfer hydrogenation using chiral Ru catalysts

The Noyori-type (1 S ,2 S )- and (1 R ,2 R )- N -( para -tosyl)-1,2-diphenylethylene-1,2-diamine ligands complexed with ruthenium have been found to be effective catalysts for the regiospecific transfer hydrogenation of 3-methoxy- and 3-benzyloxy-( Z )16-hydroxymethylidene-13α-estra-1,3,5(10)-trien-...

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Published in:Reaction kinetics, mechanisms and catalysis mechanisms and catalysis, 2018-10, Vol.125 (1), p.47-53
Main Authors: Kiss, Anita, Mernyák, Erzsébet, Wölfling, János, Szőllősi, György, Schneider, Gyula
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Chemistry and Materials Science
Industrial Chemistry/Chemical Engineering
Physical Chemistry
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Summary:The Noyori-type (1 S ,2 S )- and (1 R ,2 R )- N -( para -tosyl)-1,2-diphenylethylene-1,2-diamine ligands complexed with ruthenium have been found to be effective catalysts for the regiospecific transfer hydrogenation of 3-methoxy- and 3-benzyloxy-( Z )16-hydroxymethylidene-13α-estra-1,3,5(10)-trien-17-ones to 3-methoxy- and 3-benzyloxy-16-hydroxymethyl-13α-estra-1,3,5(10)-trien-17-one diastereomers. The ratio of the diastereomers depends on the catalyst used. Further reduction of the isolated products with NaBH 4 in the presence of cerium(III) chloride (Luche reduction conditions) yielded the corresponding diols. In contrast to the previous preparation methods, this two-step simple hydrogenation/reduction protocol afforded all four possible isomers in almost equal amounts.
ISSN:1878-5190
1878-5204
DOI:10.1007/s11144-018-1453-6