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Enantioselective Horner-Wadsworth-Emmons reaction for the asymmetric synthesis of alpha-fluoro-alpha,beta-unsaturated esters



Enantioselective Horner-Wadsworth-Emmons reaction for the asymmetric synthesis of alpha-fluoro-alpha,beta-unsaturated esters



Tetrahedron Letters 43(2): 281-284, 7 January



The enantioselective Horner-Wadsworth-Emmons reaction of 2-fluoro-2-diethylphosphonoacetates with sigma-symmetric prochiral 2-substituted-1,3-dioxan-5-ones and 4-substituted-cyclohexanones was investigated by employing Sn(OSO2CF3)2 and N-ethylpiperidine in the presence of an external chiral ligand, (S)-(-)-1-methyl-2-(1-piperidinomethyl)pyrrolidine. A chiral alpha-fluoro-alpha,beta-unsaturated ester was obtained in up to 80% ee.

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