Tetrahedron: Asymmetry

First catalytic enantioselective synthesis of the cocaine abuse therapeutic agent (S)-(+)-1-(4-{2-[bis (4-fluorophenyl) methoxy] ethyl} piperazin-1-yl)-2-phenyl-2- …

VJ Forrat, DJ Ramón, M Yus

Index: Forrat, Vicente J.; Ramon, Diego J.; Yus, Miguel Tetrahedron Asymmetry, 2007 , vol. 18, # 3 p. 400 - 405

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Citation Number: 22

Abstract

(S)-(+)-1-(4-{2-[Bis (4-fluorophenyl) methoxy] ethyl} piperazin-1-yl)-2-phenyl-2-propanol, which is a promising candidate as a cocaine abuse therapeutic agent, is prepared in several steps. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to either 2-chloro or 2-bromoacetophenone catalyzed by the use of different chiral isoborneolsulfonamide ligands in the presence of titanium tetraisopropoxide. The ...