Molecular sieves 4A work to mediate the catalytic metal enolization of nucleophile precursors: application to catalyzed enantioselective Michael addition reactions |
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| Authors: | Masayuki Hasegawa Fumiyasu Ono |
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| Institution: | a Institute for Materials Chemistry and Engineering, 6-1 Kasugakoen, Kasuga 816-8580, Japan
b Department of Molecular and Material Sciences, Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga 816-8580, Japan |
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| Abstract: | Molecular sieves 4A (MS4A) work effectively as base leading to catalytic generation of nickel(II) enolate or nitronate nucleophiles through deprotonation of the α-hydrogen atom of nucleophile precursors on treatment with a catalytic amount of chiral nickel(II) ions. The resulting reactive intermediates can be successfully trapped with α,β-unsaturated carbonyl electrophiles to produce the corresponding Michael adducts in good yields with high enantioselectivities. |
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