A lactam-derived vinyl boronate as a stable and crystalline reagent for the synthesis of 2-substituted piperidines by Pd-catalyzed coupling reactions

A Ferrali, A Guarna, FL Galbo, EG Occhiato

Index: Ferrali, Alessandro; Guarna, Antonio; Lo Galbo, Fabrizio; Occhiato, Ernesto G. Tetrahedron Letters, 2004 , vol. 45, # 27 p. 5271 - 5274

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Citation Number: 7

Abstract

A δ-valerolactam-derived vinyl triflate has been converted into the corresponding vinyl boronate by Pd-catalyzed coupling with bis (pinacolato) diboron, which results in an umpolung. This boronate efficiently couples under Pd catalysis with aryl and heteroaryl bromides to give the corresponding 2-substituted piperidines in excellent yields.