TY - JOUR
T1 - Acetals of γ-oxo-α,β-unsaturated esters in nitrone cycloadditions. Regio- and stereochemical implications
AU - Alibés, Ramon
AU - Busquè, Félix
AU - De March, Pedro
AU - Figueredo, Marta
AU - Font, Josep
AU - Gambino, Maria Esmeralda
AU - Keay, Brian A.
PY - 2001/7/16
Y1 - 2001/7/16
N2 - Several acetals of γ-oxo-α,β-unsaturated esters have been prepared, mainly from enantiopure C2-symmetric diols, and their 1,3-dipolar cycloaddition to 2,3,4,5-tetrahydropyridine 1-oxide has been studied. All the reactions showed complete regioselectivity and a high preference for the endo approach of the reactants in the transition state. The enantiopure acetals derived from (cis,cis)-spiro[4.4]nonane-1,6-diol gave the highest diastereofacial selectivity. © 2001 Elsevier Science Ltd. All rights reserved.
AB - Several acetals of γ-oxo-α,β-unsaturated esters have been prepared, mainly from enantiopure C2-symmetric diols, and their 1,3-dipolar cycloaddition to 2,3,4,5-tetrahydropyridine 1-oxide has been studied. All the reactions showed complete regioselectivity and a high preference for the endo approach of the reactants in the transition state. The enantiopure acetals derived from (cis,cis)-spiro[4.4]nonane-1,6-diol gave the highest diastereofacial selectivity. © 2001 Elsevier Science Ltd. All rights reserved.
U2 - 10.1016/S0957-4166(01)00294-4
DO - 10.1016/S0957-4166(01)00294-4
M3 - Article
SN - 0957-4166
VL - 12
SP - 1747
EP - 1756
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 12
ER -