A delta-valerolactam-derived vinyl triflate has been converted into the corresponding vinyl boronate by Pd-catalyzed coupling with bis(pinacolato)diboron, which results in all umpolung. This boronate efficiently couples under Pd catalysis with aryl and heteroaryl bromides to give the corresponding 2-substituted piperidines ill excellent yields.
A Lactam-derived Vinyl Boronate as a Stable and Crystalline Reagent for the Synthesis of 2-substituted Piperidines by Pd-catalyzed Coupling Reactions / FERRALI A.; GUARNA A.; LO GALBO F.; E. OCCHIATO. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 27:(2004), pp. 5271-5274. [10.1016/j.tetlet.2004.05.015]
A Lactam-derived Vinyl Boronate as a Stable and Crystalline Reagent for the Synthesis of 2-substituted Piperidines by Pd-catalyzed Coupling Reactions
GUARNA, ANTONIO;OCCHIATO, ERNESTO GIOVANNI
2004
Abstract
A delta-valerolactam-derived vinyl triflate has been converted into the corresponding vinyl boronate by Pd-catalyzed coupling with bis(pinacolato)diboron, which results in all umpolung. This boronate efficiently couples under Pd catalysis with aryl and heteroaryl bromides to give the corresponding 2-substituted piperidines ill excellent yields.
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