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Copper catalyzed enantioselective allylic substitution by MeMgX

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Published in Tetrahedron Letters. 2004, vol. 45, no. 39, p. 7375-7378
Abstract Methyl Grignard undergoes highly regio (>90/10) and enantioselective (ee 91–96%) copper catalyzed allylic substitution on cinnamyl-type chlorides. CuBr (3%) and 3.3% of a chiral phosphoramidite ligand are sufficient for a complete reaction. The synthesis of a precursor of (+)-Naproxen is described. The reaction can be extended to alkyl substituted allylic chlorides (ee 72%).
Keywords AsymmetryCopperCatalysisGrignard reagentAllylic substitutionNaproxen
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TISSOT-CROSET, Karine, ALEXAKIS, Alexandre. Copper catalyzed enantioselective allylic substitution by MeMgX. In: Tetrahedron Letters, 2004, vol. 45, n° 39, p. 7375-7378. https://archive-ouverte.unige.ch/unige:8120

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Deposited on : 2010-06-21

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