165306-47-8Relevant academic research and scientific papers
Facial Selectivity in Cycloadditions of a Chiral Ketene Acetal under Microwave Irradiation in Solvent-Free Conditions. Configurational Assignment of the Cycloadducts by NOESY Experiments and Molecular Mechanics Calculations
Diaz-Ortiz, Angel,Diez-Barra, Enrique,Hoz, Antonio de la,Prieto, Pilar,Moreno, Andres,et al.
, p. 4160 - 4166 (2007/10/02)
(R)-4-Phenyl-2-methylene-1,3-dioxolane (1) undergoes 1,3-dipolar and Diels-Alder cycloadditions under microwave irradiation within 3 min with excellent yields, a simple purification procedure, and an interesting facial selectivity.The stereochemistry of these cycloadducts has been inferred by NOESY experiments and molecular mechanics calculations.X-ray structure determination was required in one case.Thermal isomerization of the cycloadducts was performed affecting only the spiro-carbon.The Diels-Alder adducts in the presence of a slight amount of acid yield the corresponding open chain esters.
