An expansion of the role of the coreylink reaction for the synthesis of α-substituted carboxylic acid esters

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Abstract

The treatment of 1,2: 5,6-di-O-isopropylidene-alpha-d-ribo-hexos-3-ulose with chloroform under basic conditions has yielded the normal 3-C-trichloromethyl-alpha-D-allofuranose derivative. Under the conditions of the modified Corey - Link reaction but with a nucleophile different from the usual azide, a range of alpha-substituted carboxylic acid esters ( and one amide) has been obtained. A similar addition of bromoform to the ulose has formed the alpha-bromo methyl ester. Two attempts at forming an 'inositol alpha-amino acid' from a polyhydroxylated cyclohexanone failed.Single-crystal X-ray structure determinations are reported for (3S)- 1,2: 5,6- di-O-isopropylidene-3-C-methoxycarbonyl-3- S-phenyl-3-thio-alpha-D-ribo-hexose, ( 3S)- 1,2: 5,6- di-O-isopropylidene-3-S-phenyl-3-C-(phenylthio)carbonyl-3- thio-alpha-d-ribo-hexose,3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methoxycarbonyl-alpha-D-erythro-hex-3-enofuranose, 4,6- di-O-benzyl-2-C-trichloromethyl-scyllo-inositol1,3,5-orthoformate,2,2'-anhydro-4,6-di-Obenzyl-2- C-dichlorohydroxymethyl-scyllo-inositol 1,3,5-orthoformate, 1,3,4,5,6- penta-O-benzyl-2-C- trichloromethylmyo- inositol, and 2-amino-1,3,4,5,6-penta-O-benzyl-2-C-cyano-2-deoxy-myo-inositol.
Original languageEnglish
Pages (from-to)426-433
JournalAustralian Journal of Chemistry
Volume59
Issue number7
DOIs
Publication statusPublished - 2006

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