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Asymmetric synthesis of esomeprazole

Cotton, Hanna ; Elebring, Thomas ; Larsson, Magnus ; Li, Lanna ; Sörensen, Henrik ; von Unge, Sverker

Tetrahedron: asymmetry, 2000-09, Vol.11 (18), p.3819-3825 [Periódico revisado por pares]

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Título:
Asymmetric synthesis of esomeprazole
Autor: Cotton, Hanna ; Elebring, Thomas ; Larsson, Magnus ; Li, Lanna ; Sörensen, Henrik ; von Unge, Sverker
É parte de: Tetrahedron: asymmetry, 2000-09, Vol.11 (18), p.3819-3825
Descrição: A highly efficient synthesis of esomeprazole—the ( S)-enantiomer of omeprazole—via asymmetric oxidation of prochiral sulphide 1 is described. The asymmetric oxidation was achieved by titanium-mediated oxidation with cumene hydroperoxide (CHP) in the presence of ( S, S)-diethyl tartrate [( S, S)-DET]. The enantioselectivity was provided by preparing the titanium complex in the presence of 1 at an elevated temperature and/or during a prolonged preparation time and by performing the oxidation of 1 in the presence of an amine. An enantioselectivity of >94% ee was obtained using this method.
Editor: Elsevier Ltd
Idioma: Inglês

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