Addition of malonyl radicals to glycals with C-1 acceptor groups: remarkable influence of the substituents on the product distributionElectronic supplementary information (ESI) available: NMR data for C-2 branched sugar derivatives. See http://www.rsc.org/suppdata/cc/b2/b202898k/ | Zendy

Viktor Gyóllai | Zendy; Dirk Schanzenbach | Zendy; László Somsák | Zendy; Torsten Linker | Zendy

Open Access

Addition of malonyl radicals to glycals with C-1 acceptor groups: remarkable influence of the substituents on the product distributionElectronic supplementary information (ESI) available: NMR data for C-2 branched sugar derivatives. See http://www.rsc.org/suppdata/cc/b2/b202898k/

Author(s) -

Viktor Gyóllai,

Dirk Schanzenbach,

László Somsák,

Torsten Linker

Publication year - 2002

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/b202898k

Subject(s) - chemistry , radical , anomer , ceric ammonium nitrate , dimethyl malonate , malonate , medicinal chemistry , organic chemistry , acceptor , ammonium nitrate , product distribution , catalysis , palladium , physics , grafting , condensed matter physics , polymer

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.

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