Stereospecific Synthesis of α-Hydroxy-Cyclopropylboronates from Allylic Epoxides.

Stereospecific Synthesis of α-Hydroxy-Cyclopropylboronates from Allylic Epoxides.
Angew Chem Int Ed Engl. 2019 Jan 02;:
Authors: Tortosa M, Amenós L, Trulli L, Nóvoa L, Parra A
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.
PMID: 30600867 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - January 2, 2019 Category: Chemistry Authors: Tortosa M, Amenós L, Trulli L, Nóvoa L, Parra A Tags: Angew Chem Int Ed Engl Source Type: research