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Synthesis and use of a phosphoramidite ligand for the copper-catalyzed enantioselective allylic substitution. Tandem allylic substitution-ring closing metathesis

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Published in Synthesis. 2004, no. 15, p. 2586-2590
Abstract A new one-pot method of reductive amination is used to prepare a chiral C2 symmetrical amine. This amine is used for the synthesis of a new chiral phosphoramidite ligand. The new ligand is, in turn, used to illustrate the enantioselective copper-catalyzed allylic substitution with Grignard reagents. When a remote double bond is located on the Grignard reagent, the newly formed alkene undergoes an in situ ruthenium-catalyzed ring-closing metathesis to afford the cyclized product in 77% yield and 94% ee.
Keywords Allylic substitutionCopper catalysisRuthenium catalysisEnantioselectivityGrignard reagents
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TISSOT-CROSET, Karine et al. Synthesis and use of a phosphoramidite ligand for the copper-catalyzed enantioselective allylic substitution. Tandem allylic substitution-ring closing metathesis. In: Synthesis, 2004, n° 15, p. 2586-2590. https://archive-ouverte.unige.ch/unige:8110

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Deposited on : 2010-06-21

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