Addition of malonyl radicals to glycals with C-1 acceptor groups

Remarkable influence of the substituents on the product distribution

Viktor Gyóllai, Dirk Schanzenbach, L. Somsák, Torsten Linker

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The ceric(IV) ammonium nitrate (CAN)-mediated radical addition of dimethyl malonate to glycals 1 affords methyl glycosides 2 and ortho esters 3 as main products; the product distribution strongly depends on the substitution pattern at the 1-position, which can be rationalized in terms of the oxidation potentials of the intermediary anomeric radicals.

Original languageEnglish
Pages (from-to)1294-1295
Number of pages2
JournalChemical Communications
Issue number12
Publication statusPublished - 2002

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Glycosides
Nitrates
Esters
Substitution reactions
Oxidation
ammonium nitrate
methyl malonate

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Addition of malonyl radicals to glycals with C-1 acceptor groups : Remarkable influence of the substituents on the product distribution. / Gyóllai, Viktor; Schanzenbach, Dirk; Somsák, L.; Linker, Torsten.

In: Chemical Communications, No. 12, 2002, p. 1294-1295.

Research output: Contribution to journalArticle

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