TY - JOUR
T1 - Stereochemical study on the cycloaddition of a cyclic nitrone to 5‐methyl‐2(5H)‐furanone
AU - Figueredo, Marta
AU - Font, Josep
AU - De March, Pedro
PY - 1989/1/1
Y1 - 1989/1/1
N2 - The 1,3‐Dipolar cycloaddition of 3,4,5,6‐tetrahydropyridine 1‐oxide (1) to 5‐methyl‐2(5H)‐furanone (2) yields adducts 3, 4, and 5, whose stereochemistry has been established by a detailed study of their low‐temperature 1H‐NMR spectra. The major adduct, 4, arises from an exo transition state and an anti approach, indicating the dominance of steric factors over secondary orbital interactions. Copyright © 1989 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
AB - The 1,3‐Dipolar cycloaddition of 3,4,5,6‐tetrahydropyridine 1‐oxide (1) to 5‐methyl‐2(5H)‐furanone (2) yields adducts 3, 4, and 5, whose stereochemistry has been established by a detailed study of their low‐temperature 1H‐NMR spectra. The major adduct, 4, arises from an exo transition state and an anti approach, indicating the dominance of steric factors over secondary orbital interactions. Copyright © 1989 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
KW - 1,3‐Dipolar cycloaddition
KW - 3,4,5,6‐Tetrahydropyridine 1‐oxide
KW - 5‐Methyl‐2(5H)‐furanone
KW - Methyl sorbate
U2 - 10.1002/cber.19891220916
DO - 10.1002/cber.19891220916
M3 - Article
SN - 0009-2940
VL - 122
SP - 1701
EP - 1704
JO - Chemische Berichte
JF - Chemische Berichte
IS - 9
ER -