Experimental and theoretical study of a Diels-Alder reaction between a sugar-derived nitroalkene and cyclopentadiene

María I Mangione; Ariel M Sarotti; Alejandra G Suárez; Rolando A Spanevello

doi:10.1016/j.carres.2010.12.006

Experimental and theoretical study of a Diels-Alder reaction between a sugar-derived nitroalkene and cyclopentadiene

Carbohydr Res. 2011 Mar 1;346(4):460-4. doi: 10.1016/j.carres.2010.12.006. Epub 2010 Dec 13.

Authors

María I Mangione¹, Ariel M Sarotti, Alejandra G Suárez, Rolando A Spanevello

Affiliation

¹ Instituto de Química de Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, Rosario, Argentina.

PMID: 21272863
DOI: 10.1016/j.carres.2010.12.006

Abstract

The Diels-Alder reaction of a pyranose-derived nitroalkene 1 with cyclopentadiene is described, and the unexpected facial selectivity of the cycloaddition is analyzed by a computational study.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Carbohydrates / chemistry*
Cyclopentanes / chemistry*
Models, Chemical
Molecular Structure
Nitro Compounds / chemistry*
Stereoisomerism

Substances

Bridged Bicyclo Compounds, Heterocyclic
Carbohydrates
Cyclopentanes
Nitro Compounds