Application of amide-stabilized sulfur ylide reactivity to the stereodivergent synthesis of (R,S)- and (S,R)-reboxetine |
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| Authors: | David M Aparicio Joel L Terán Dino Gnecco Alberto Galindo Jorge R Juárez María L Orea Angel Mendoza |
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| Institution: | Centro de Química. Benemérita Universidad Autónoma de Puebla, Edif. 194 Complejo de Ciencias, C. U., 72570 Puebla, Pue., Mexico |
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| Abstract: | A simple access to (R,S)- and (S,R)-reboxetine from a single chiral sulfonium salt 4 is reported. This approach, based on a stabilized sulfur ylide-mediated epoxidation, followed by a regioselective opening reaction, enables the preparation of these two potentially biologically active compounds in 35.6% and 13.7% overall yield. |
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