TY - JOUR
T1 - First example of a third generation nitrone cycloaddition
AU - De March, Pedro
AU - Figueredo, Marta
AU - Font, Josep
AU - Milán, Sergio
AU - Alvarez-Larena, Angel
AU - Piniella, Juan F.
AU - Molins, Elies
PY - 1997/2/24
Y1 - 1997/2/24
N2 - Compounds 5 and 6, derived from the cycloadditions of a nitrone to α,β-unsaturated lactones, were oxidized with m-chloroperbenzoic acid affording regiospecifically aldonitrones, 8 and 14, respectively. These second generation nitrones were reacted with several dipolarophiles yielding cycloadducts 9-13, 15, and 16. A repeated sequence of oxidation-cycloaddition applied to compound 12 allowed the isolation of die first example of a third generation cycloadduct, 17. During this work a series of new highly functionalized pyrrolidines have been prepared.
AB - Compounds 5 and 6, derived from the cycloadditions of a nitrone to α,β-unsaturated lactones, were oxidized with m-chloroperbenzoic acid affording regiospecifically aldonitrones, 8 and 14, respectively. These second generation nitrones were reacted with several dipolarophiles yielding cycloadducts 9-13, 15, and 16. A repeated sequence of oxidation-cycloaddition applied to compound 12 allowed the isolation of die first example of a third generation cycloadduct, 17. During this work a series of new highly functionalized pyrrolidines have been prepared.
U2 - 10.1016/S0040-4020(96)01177-5
DO - 10.1016/S0040-4020(96)01177-5
M3 - Article
SN - 0040-4020
VL - 53
SP - 2979
EP - 2988
JO - Tetrahedron
JF - Tetrahedron
IS - 8
ER -