Issue 7, 2010
From the journal:

Organic & Biomolecular Chemistry

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

Marcelo T. de Oliveira,*ab   Amary Cesar,a   Daniel H. S. Leal,b   Maria A. F. Prado,b   Thais H. Á. da Silvab  and  Ricardo J. Alvesb  

* Corresponding authors

a Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte, MG, Brazil
E-mail: mtavares@netuno.lcc.ufmg.br

b Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte, MG, Brazil

Abstract

A computational investigation on the origin of the stereoselectivity of 6-exo-trig radical cyclization of α,β-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.

Graphical abstract: Unravelling the stereoselectivity in 6-exo-trig radical cyclization of α,β-unsaturated ester-tethered sugars. A tale of two stereocenters

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Article information

DOI
https://doi.org/10.1039/B923414D
Article type
Paper
Submitted
18 Nov 2009
Accepted
06 Jan 2010
First published
01 Feb 2010

Org. Biomol. Chem., 2010,8, 1619-1622

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

M. T. de Oliveira, A. Cesar, D. H. S. Leal, M. A. F. Prado, T. H. Á. da Silva and R. J. Alves, Org. Biomol. Chem., 2010, 8, 1619 DOI: 10.1039/B923414D

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