Unravelling the stereoselectivity in 6-exo-trig radical cyclization of alpha,beta-unsaturated ester-tethered sugars. A tale of two stereocenters

A computational investigation on the origin of the stereoselectivity of 6-exo-trig radical cyclization of alpha,beta-unsaturated ester-tethered sugars has revealed that a boat-like transition state, which keeps the ester in a planar conformation, holds the chiral information. Following this model, t...

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Published inOrganic & biomolecular chemistry Vol. 8; no. 7; pp. 1619 - 1622
Main Authors de Oliveira, Marcelo T, Cesar, Amary, Leal, Daniel H S, Prado, Maria A F, da Silva, Thais H A, Alves, Ricardo J
Format Journal Article
LanguageEnglish
Published England 01.01.2010
Subjects
Carbohydrates - chemistry
Cyclization
Esters - chemistry
Models, Molecular
Stereoisomerism
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Summary:A computational investigation on the origin of the stereoselectivity of 6-exo-trig radical cyclization of alpha,beta-unsaturated ester-tethered sugars has revealed that a boat-like transition state, which keeps the ester in a planar conformation, holds the chiral information. Following this model, the stereocenter to which the ester functionality is connected reports the chirality to the newly formed stereocenter via a 1,4-transfer mechanism.
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ISSN:1477-0520
1477-0539
DOI:10.1039/b923414d