6533b82cfe1ef96bd128f460

RESEARCH PRODUCT

An AM1 study on π-facial selectivity in Diels-Alder reactions of 2-aza-1, 3-dienes with azodienophiles

Santos FusteroJosé A. SordoJosé BarluengaJavier GonzálezTomás L. Sordo

subject

chemistry.chemical_compoundDienechemistryComputational chemistryDiimideDiels alderOrganic chemistryStereoselectivityPhysical and Theoretical ChemistryCondensed Matter PhysicsSelectivityBiochemistry

description

Abstract A theoretical study of the π-facial selectivity in Diels-Alder reactions of chloro derivatives of 2-aza-1,3-dienes with azodienophiles has been carried out using the semiempirical AM1 method. Three transition structures for the model reaction of the diene 3 with the dienophile 4 were located. The Diels-Alder reaction of the non-substituted 2-aza-1,3-diene 6 with the trans -diimide was studied. All transition structures located show an important asynchronicity and the calculations reveal the presence of stereoelectronic effects. The predicted stereoselectivity is in agreement with the experimental evidence.

yearjournalcountryeditionlanguage
1994-12-01Journal of Molecular Structure: THEOCHEM
https://doi.org/10.1016/0166-1280(94)03774-f