Allenyl sulfones and allenyl sulfides in the synthesis of 3-pyrrolines. A novel nucleophilic [3 + 2] cycloaddition on allenyl sulfones giving rearranged cycloadducts.
Efficient methodologies for the synthesis of regioisomeric 3-pyrrolines by reaction of electron-deficient imines and sulfur-containing allenyl derivatives are presented. Lithiated thioallenes give 2-aryl-3-phenylsulfonyl-3-pyrrolines, whereas allenyl sulfones furnish the isomeric 2-aryl-4-phenylsulfonyl-3-pyrrolines through migration of the sulfonyl group that catalyzes the nucleophilic [3 + 2] cycloaddition.
Moreno-Clavijo
Elena
E
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, 1, E-41012 Seville, Spain.
Carmona
Ana T
AT
Reissig
Hans-Ulrich
HU
Moreno-Vargas
Antonio J
AJ
Alvarez
Eleuterio
E
Robina
Inmaculada
I
D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010675:Pheromones / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*
D007097:Imines; D010675:Pheromones; D011758:Pyrroles; D013440:Sulfides; D013450:Sulfones; C013231:pyrroline