Palladium(0)-catalyzed cross-coupling of potassium (Z)-2-chloroalk-1-enyl trifluoroborates: a chemo- and stereoselective access to (Z)-chloroolefins and trisubstituted alkenes. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2009

Palladium(0)-catalyzed cross-coupling of potassium (Z)-2-chloroalk-1-enyl trifluoroborates: a chemo- and stereoselective access to (Z)-chloroolefins and trisubstituted alkenes.

Résumé

We describe the preparation of a series of new potassium trifluoroborates 1 and the study of their behaviour in a Pd(0)-catalyzed cross-coupling reaction. We found that compounds 1 are endowed with original properties as they behave as nucleophilic cross-coupling partners chemoselectively but also as ambivalent synthons. The usefulness of this methodology has been successfully illustrated by the first total synthesis of an N-acyl spermidine.
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Dates et versions

hal-00396313 , version 1 (17-06-2009)

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Xavier Guinchard, Xavier Bugaut, Cyril Cook, Emmanuel Roulland. Palladium(0)-catalyzed cross-coupling of potassium (Z)-2-chloroalk-1-enyl trifluoroborates: a chemo- and stereoselective access to (Z)-chloroolefins and trisubstituted alkenes.. Chemistry - A European Journal, 2009, 15 (23), pp.5793-8. ⟨10.1002/chem.200900425⟩. ⟨hal-00396313⟩
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