2,3:4,5-DI-O-isopropylidene-β-D-fructopyranose as chiral auxiliary in asymmetric α-alkylation of ester enolates

Article abstract of DOI:10.1080/07328309608005685

The asymmetric α-alkylation of enolates of chiral esters derived from 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose (1) was studied. The diastereoselectivities range from 1:1 to 7:3. The absolute stereochemistry of the major S-isomers were established by chemical correlation. The diastereoselectivities of the alkylated products were similar to those observed in the deprotonation steps. The stereochemical outcome can be interpreted by an intramolecular complexation of the lithium cation of the carbohydrate ester enolates.

Full text of DOI:10.1080/07328309608005685

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Journal of Carbohydrate Chemistry
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2,3:4,5-DI-O-Isopropylidene-β-d-
Fructopyranose as Chiral Auxiliary
in Asymmetric α-Alkylation Of Ester
Enolates
Paulo R.R. Costa a , Vitor F. Ferreira b , Karla G. Alencar a , Hiran
C.A. Filho a , Claudio M. Ferreira a & Sergio Pinheiro a
a Núcleo de Pesquisas de Produtos Naturais - Universidade Federal
do Rio de Janeiro , CCS-Bloco H, CEP 21941, Rio de Janeiro, Brazil
b Universidade Federal Fluminense, Departamento de Química
Org[acaron]nica , Niterói, CEP 24210-150, RJ, Brazil
Published online: 22 Aug 2006.
To cite this article: Paulo R.R. Costa , Vitor F. Ferreira , Karla G. Alencar , Hiran C.A. Filho , Claudio
M. Ferreira & Sergio Pinheiro (1996) 2,3:4,5-DI-O-Isopropylidene-β-d-Fructopyranose as Chiral
Auxiliary in Asymmetric α-Alkylation Of Ester Enolates, Journal of Carbohydrate Chemistry, 15:6,
691-699, DOI: 10.1080/07328309608005685
To link to this article: http://dx.doi.org/10.1080/07328309608005685
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