Stereospecific Synthesis of α‐Hydroxy‐Cyclopropylboronates from Allylic Epoxides

Abstract

Herein, we report a catalytic and stereospecific method for the preparation of enantioenriched a-hydroxy cyclopropylboronates with control in four contiguous stereocenters. The reaction involves the borylation of readily available allylic epoxides using an inexpensive Cu(I) salt and a commercially available phosphine ligand. High diastereocontrol is achieved and different diastereomers can be selectively prepared. Functionalization of the carbon-boron bond provides access to different enantiomerically enriched trisubstituted cyclopropanes from a common intermediate.

Facile synthesis of alkyl- and arylboronate esters enabled by a carbon nanotube supported copper catalyst

“…Arylboronate esters are of great importance in organic synthesis, particularly in transition-metal-catalysed C–C, C–O and C–N bond-forming reactions, as exemplified by the Suzuki–Miyaura cross-coupling reaction. 1,45 While Cu/N-CNT NPs worked in the reaction (see ESI†), Cu/CNT NPs offered the optimal combination of reactivity. Aryl halides with different electronic properties, as well as different halogen substituents, were investigated (Table 6).…”