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Grignard reagents react with epoxides and dissolve in THF what about oxetane?
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Mechael Kanovsky
Grignard reagents react with epoxides and dissolve in THF what about oxetane?
Grignard reagents react slowly with oxetanes to afford primary alcohols after acidic workup. Application of heat accelerates this reaction.
Better way: Reactions of Grignard reagents with oxetanes when performed in the presence of copper catalysts proceed under mild conditions and afford the corresponding primary alcohol in good yield. Reference: Huynh, C.; Derguini-Boumechal, F.; Linstrumelle, G. Tetrahedron Lett.1979, 20, 1503-1506.
Enantioselective opening of oxetanes has been achieved by the combination of a chiral ether and phenyllithium in the presence of boron trifluoride to give the corresponding alcohol in 47% ee. Reference: Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron Asymmetry1996, 7, 2483-2484.
Grignard reagents react slowly with oxetanes to afford primary alcohols after acidic workup. Application of heat accelerates this reaction.
Better way: Reactions of Grignard reagents with oxetanes when performed in the presence of copper catalysts proceed under mild conditions and afford the corresponding primary alcohol in good yield. Reference: Huynh, C.; Derguini-Boumechal, F.; Linstrumelle, G. Tetrahedron Lett.1979, 20, 1503-1506.
Enantioselective opening of oxetanes has been achieved by the combination of a chiral ether and phenyllithium in the presence of boron trifluoride to give the corresponding alcohol in 47% ee. Reference: Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron Asymmetry1996, 7, 2483-2484.
Better way: Reactions of Grignard reagents with oxetanes when performed in the presence of copper catalysts proceed under mild conditions and afford the corresponding primary alcohol in good yield. Reference: Huynh, C.; Derguini-Boumechal, F.; Linstrumelle, G. Tetrahedron Lett. 1979, 20, 1503-1506.
Enantioselective opening of oxetanes has been achieved by the combination of a chiral ether and phenyllithium in the presence of boron trifluoride to give the corresponding alcohol in 47% ee. Reference: Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron Asymmetry 1996, 7, 2483-2484.
Better way: Reactions of Grignard reagents with oxetanes when performed in the presence of copper catalysts proceed under mild conditions and afford the corresponding primary alcohol in good yield. Reference: Huynh, C.; Derguini-Boumechal, F.; Linstrumelle, G. Tetrahedron Lett. 1979, 20, 1503-1506.
Enantioselective opening of oxetanes has been achieved by the combination of a chiral ether and phenyllithium in the presence of boron trifluoride to give the corresponding alcohol in 47% ee. Reference: Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron Asymmetry 1996, 7, 2483-2484.
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