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Stereoselective synthesis of polyhydroxylated pyrrolidines: a route to novel 3,5-bis(hydroxymethyl)pyrrolidines from 2-azabicyclo[2.2.1]hept-5-enes |
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| Authors: | M. José Alves,M. Luisa C. Vale,Fá bio R. Aguiar |
| Affiliation: | a Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal b Dpto. Química Orgánica, Fac. Farmacia, Universidade de Santiago de Compostela. E-15782 Santiago de Compostela, Spain c CIQ, Dpto. Química, Fac. Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal |
| Abstract: | An efficient preparation of racemic and chiral 2-functionalized-3,5-bis(hydroxymethyl)pyrrolidines is described. The method uses 2-azabicyclo[2.2.1]hept-5-enes, readily obtained from glyoxylates of aliphatic amines and cyclopentadiene, as starting material. The hydroxylation of the double bond followed by the oxidative cleavage of the six-membered ring and in situ reduction of the dialdehyde intermediate gives the title pyrrolidines. |
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