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A Convergent, Stereoselective Route to Trisubstituted Alkenyl Boronates

Abstract : A modular, stereoselective route to trisubstituted (Z)-alkenyl (MIDA)boronates is described, consisting of the radical addition–fragmentation of dithiocarbonates to 2-(MIDA)boronyl-3-(2′-fluoro-pyridyl-6′-oxy)-alkenes. The bulky (MIDA)boronate ensures a highly stereoselective fragmentation that is enhanced by the poor stabilization of the radical adjacent to the tetravalent boron atom. The vinyl boronate precursors are prepared from propargyl alcohols by copper-catalyzed regioselective protoboration of their fluoropyridoxy derivatives, with the fluoropyridine acting as an internal directing group
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https://hal.archives-ouvertes.fr/hal-03416821
Contributor : Samir Zard Connect in order to contact the contributor
Submitted on : Friday, November 5, 2021 - 1:04:45 PM
Last modification on : Tuesday, January 4, 2022 - 5:55:38 AM

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Jean Michalland, Samir Zard. A Convergent, Stereoselective Route to Trisubstituted Alkenyl Boronates. Organic Letters, American Chemical Society, 2021, 23 (20), pp.8018-8022. ⟨10.1021/acs.orglett.1c03022⟩. ⟨hal-03416821⟩

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