Chromatography-free product separation in the Mitsunobu reaction

Products can easily be isolated in generally excellent yields from Mitsunobu reactions without resort to chromatography by prior oxidation using dilute hydrogen peroxide followed by simple filtrations through silica gel and aqueous washings. Mitsunobu products can be isolated pure without column chr...

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Bibliographic Details
Published in:Tetrahedron letters 2006-07, Vol.47 (29), p.5151-5154
Main Authors: Proctor, Anthony J., Beautement, Kevin, Clough, John M., Knight, David W., Li, Yingfa
Format: Article
Language:English
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Summary:Products can easily be isolated in generally excellent yields from Mitsunobu reactions without resort to chromatography by prior oxidation using dilute hydrogen peroxide followed by simple filtrations through silica gel and aqueous washings. Mitsunobu products can be isolated pure without column chromatography by first washing a solution of the crude reaction mixture in dichloromethane with 15% aqueous hydrogen peroxide followed by aqueous sodium sulfite. A final filtration through silica gel secures the pure Mitsunobu product.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.05.070