diastereoselective intramolecular Alder-Ene reaction on chiral perhydro-1,3-benzoxazines. a rapid entry to enantiopure cis-3,4-disubstituted pyrrolidines |
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| Authors: | Pedrosa Rafael Andrés Celia Martín Laura Nieto Javier Rosón Carlos |
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| Institution: | Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011 Valladolid, Spain. pedrosa@qo.uva.es |
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| Abstract: | 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. |
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