The regiochemistry and stereochemistry of 1,3-dipolar cycloaddition of cyclic nitrones |
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| Institution: | 1. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University, Changsha 410081, China;2. Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, China;3. Beijing National Laboratory for Molecular Sciences (BNLMS), Peking University, Beijing 100871, PR China;1. Universidad de Valencia, Departamento de Química Orgánica, Dr. Moliner 50, E-46100 Burjassot, Valencia, Spain;2. Universidad Andres Bello, Facultad de Ciencias Exactas, Departamento de Ciencias Químicas, Laboratorio de Química Teórica, Av. República 230, 8370146 Santiago, Chile;2. Ingénierie et Architectures Macromoléculaires, Institut Charles Gerhardt UMR – CNRS 5253, 8, Rue de l’école Normale, ENSCM, 34296 Montpellier, France |
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| Abstract: | A comparative study of the regio- and stereo-chemical behaviour of the 1,3-dipolar cycloaddition of a series of alkenes with 1-pyrroline 1-oxide and 2,3,4,5-tetrahydropyridine 1-oxide has been carried out. The high degree of both regio- and stereochemical control observed in these reactions has been explained in terms of frontier orbital interaction, steric factors, and secondary orbital interaction in the transition state. While most common alkenes (both mono- and 1,1-di-substituted) gave 2-substituted cycloadducts, highly polarized alkene dimethyl methylenemalonate afforded mainly regioisomeric 3-substituted cycloadduct. Significant secondary orbital interaction is observed with the non-conjugated substituents, hydroxymethyl and its derivatives. |
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