Issue 12, 2002
From the journal:

Chemical Communications

Addition of malonyl radicals to glycals with C-1 acceptor groups: remarkable influence of the substituents on the product distribution†

Viktor Gyóllai,a   Dirk Schanzenbach,b   László Somsák*a  and  Torsten Linker*b  

* Corresponding authors

a Department of Organic Chemistry, University of Debrecen, PO Box 20, Debrecen, Hungary
E-mail: somsak@tigris.klte.hu
Fax: +36-52-453-836
Tel: +36-52-512-900/2348

b Department of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, Golm, Germany
E-mail: linker@chem.uni-potsdam.de
Fax: +49-331-977-5056
Tel: +49-331-977-5212

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.

Graphical abstract: Addition of malonyl radicals to glycals with C-1 acceptor groups: remarkable influence of the substituents on the product distribution

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Article information

DOI
https://doi.org/10.1039/B202898K
Article type
Communication
Submitted
22 Mar 2002
Accepted
09 May 2002
First published
17 May 2002

Chem. Commun., 2002, 1294-1295

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Addition of malonyl radicals to glycals with C-1 acceptor groups: remarkable influence of the substituents on the product distribution

V. Gyóllai, D. Schanzenbach, L. Somsák and T. Linker, Chem. Commun., 2002, 1294 DOI: 10.1039/B202898K

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