Asymmetric cyanosilylation of ketones catalyzed by recyclable polymer-supported copper(II) salen complexes |
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Authors: | Gurusamy Rajagopal Shanmugam Selvaraj Karuthamohamed Dhahagani |
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Institution: | Department of Chemistry, Government Arts College, Melur 625 106, Madurai, India |
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Abstract: | Various ketones have undergone asymmetric trimethylsilylcyanation at room temperature with (CH3)3SiCN (TMSCN) in the presence of a chiral-supported Cu(salen) complex and Ph3PO as the catalyst. Aromatic, aliphatic, and heterocyclic ketones have been converted into the corresponding cyanohydrin trimethylsilyl ethers in 83?96% yields with 52?84% ee. Several factors concerning the reactivity and enantioselectivity have been discussed. A double activation where Cu(salen) plays the role of Lewis acid and Ph3PO acts as a Lewis base is reported. Poly(ethylene glycol) monomethyl ether (MeO-PEG) has been used as a soluble support while JandaJel (JJ) and Merrifield (MF) resins served as insoluble supports. Each polymer is linked to the salen catalyst through a glutarate spacer. The soluble catalysts were recovered by precipitation with a suitable solvent while the insoluble catalysts were simply filtered from the reaction mixture. The JandaJel-attached Cu(salen) catalyst could be used for five cycles with the retention of efficiency and the Merrifield-bound Cu(salen) catalyst was found to loose activity with each use. |
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