Tetrahedron p. 13633 - 13640 (1997)
Update date:2022-07-30
Topics:
Otera, Junzo
Nakazawa, Koichi
Sekoguchi, Koichi
Orita, Akihiro
Clean inversion of secondary mesylates and tosylates is effected by CsF in DMF. A variety of oxygen-, sulfur-, nitrogen-, and carbon-nucleophiles are employable. The reaction conditions have been optimized. The use of CsF in DMF is crucial and the reaction proceeds on the surface of solid CsF. It is suggested that hydrogen bonding between CsF and an active hydrogen of nucleophiles is responsible for the smooth reaction. Cesium carbonate fails to give rise to high specificity of inversion indicative of superiority of CsF.
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