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

Research output: Contribution to journalArticle

Abstract

The Noyori-type (1S,2S)- and (1R,2R)-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 NaBH4 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.

Original languageEnglish
Pages (from-to)47-53
Number of pages7
JournalReaction Kinetics, Mechanisms and Catalysis
Volume125
Issue number1
DOIs
Publication statusPublished - Oct 1 2018

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Keywords

  • Asymmetric catalysis
  • Ruthenium
  • Steroid
  • Transfer hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

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