Hydrogenolysis of the 4,6-o-ketals of glucopyranosides. Configuration-dependent high regio- and stereo-selectivity of the diastereoisomeric acetophenone derivatives

János Hajkó, Gabriella Szabovik, János Kerékgyártó, Márton Kajtár, András Lipták

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Abstract

Hydrogenolysis (reductive cleavage) of the (R) isomers of the acetophenone 4,6-O-derivatives of glucopyranosides with LiAlH4/AlCl3 gives the 4-O-(1′-phenylethyl) ethers with (R) configuration; the corresponding (5) isomers produce the respective (R) 6-O-(1′-phenylethyl) ethers are produced. The hydrogenolysis of other 4,6-O-ketals affords O 4 ether derivatives; the two diastereoisomeric 4,6-O-s-butylidene derivatives (cyclic ketals) give O 4-ethers with the opposite absolute configuration. The stereoselectivity of these reactions is explained by the development of a four-centre transition state. The absolute configuration of the ethers has been determined by means of circular dichroism measurements.

Original languageEnglish
Pages (from-to)357-363
Number of pages7
JournalAustralian Journal of Chemistry
Volume49
Issue number3
DOIs
Publication statusPublished - Jan 1 1996

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ASJC Scopus subject areas

  • Chemistry(all)

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