Stereospecific Synthesis of α‐Hydroxy‐Cyclopropylboronates from Allylic Epoxides

Rigid sp³ scaffolds: A catalytic and stereospecific method for the preparation of enantioenriched α‐hydroxy cyclopropylboronates with control in four contiguous stereocenters is described. 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.

Abstract

Herein, we report a catalytic and stereospecific method for the preparation of enantioenriched α‐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.

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