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Pd-catalyzed cross-coupling reaction of (Z)- and (E)-bromoenyne: unusual stereochemical outcome
Authors:Jun&rsquo  ichi Uenishi,Katsuaki Matsui,Masashi Ohmi
Affiliation:Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan
Abstract:Pd-catalyzed cross-coupling reaction of (E)-bromoenyne 1Z with 1-alkyne and tributylvinyl-stannane occurs with retention of the configuration in benzene but with an inversion of the configuration in DMF or CH2Cl2. On the other hand, that of (Z)-bromoenyne 1E occurs with retention of the configuration in these solvents.
Keywords:Bromoenyne   Sonogashira coupling   Stille coupling, Enediyne   Stereocontrol
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