A Convergent, Stereoselective Route to Trisubstituted Alkenyl Boronates

Jean Michalland (1) , Samir Zard (1)

1 DCSO - Laboratoire de synthèse organique

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

Domaines: Chimie organique

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