TY - JOUR
T1 - Diastereofacial selectivity in the cycloaddition of nitrones to (E)-γ-oxygenated α,β-unsaturated esters
AU - Busqué, Félix
AU - De March, Pedro
AU - Figueredo, Marta
AU - Font, Josep
AU - Monsalvatje, Montserrat
AU - Virgili, Albert
AU - Álvarez-Larena, Ángel
AU - Piniella, Juan F.
PY - 1996/11/29
Y1 - 1996/11/29
N2 - The 1,3-dipolar cycloadditions of nitrones 1 and 2 to a series of 1,2-disubstituted electron-deficient olefins bearing an allylic stereocenter, 4-8, are reported. The syn/anti stereochemistry of the major endo adducts may be rationalized through the Houk transition-state model, but the possibility of intramolecular hydrogen bonding must be taken into account. In the case of the minor exo adducts the syn stereochemistry always predominates.
AB - The 1,3-dipolar cycloadditions of nitrones 1 and 2 to a series of 1,2-disubstituted electron-deficient olefins bearing an allylic stereocenter, 4-8, are reported. The syn/anti stereochemistry of the major endo adducts may be rationalized through the Houk transition-state model, but the possibility of intramolecular hydrogen bonding must be taken into account. In the case of the minor exo adducts the syn stereochemistry always predominates.
M3 - Article
SN - 0022-3263
VL - 61
SP - 8578
EP - 8585
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -