diastereoselective intramolecular Alder-Ene reaction on chiral perhydro-1,3-benzoxazines. a rapid entry to enantiopure cis-3,4-disubstituted pyrrolidines.
Chiral 3-acryloyl-2-vinyl-substituted 1,3-perhydrobenzoxazines derived from (-)-8-aminomenthol participate in an ene reaction leading to 3,4-disubstituted pyrrolidinone derivates with excellent diastereoselectivity. The cycloadducts were transformed into enantiopure 3,4-disubstituted pyrrolidines after elimination of the chiral adjuvant.
Pedrosa
Rafael
R
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011 Valladolid, Spain. pedrosa@qo.uva.es
Andrés
Celia
C
Martín
Laura
L
Nieto
Javier
J
Rosón
Carlos
C