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Synlett 1999; 1999(10): 1539-1542
DOI: 10.1055/s-1999-2883
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Electrophilic Substitutions of 1-Alkenylcyclopropyl Esters: Diethylzinc-Mediated Umpolung of π-1,1-Dimethyleneallyl Palladium Complexes

Jean Ollivier* , Nicolas Girard, Jacques Salaün
  • *Laboratoire des Carbocycles (Associé au CNRS), Institut de Chimie Moléculaire d'Orsay, Bât. 420, Université de Paris-Sud, 91405 ORSAY, France; Fax + 33(1)69 15 62 78; E-mail: jasalaün@icmo.u-psud.fr
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Publication Date:
31 December 1999 (online)

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1-Ethenylcyclopropyl sulfonates underwent regioselective electrophilic γ-substitution by carbonyl compounds in the presence of palladium(0) (5%) and of diethylzinc (2 equiv), to provide 3-cyclopropylidenepropan-1-ol derivatives in high yields (74-85%); however, the α-substitution which led to 1-ethenylcyclopropylcarbinol derivatives was governed by the trialkylsilyl substituent effect.

1,1-dimethyleneallyl zinc complexes - regioselective α- and γ-electrophilic substitutions - 3-cyclopropylidenepropan-1-ols

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