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Stereospecific Synthesis of α‐Hydroxy‐Cyclopropylboronates from Allylic Epoxides
Author(s) -
Amenós Laura,
Trulli Laura,
Nóvoa Luis,
Parra Alejandro,
Tortosa Mariola
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812836
Subject(s) - stereocenter , allylic rearrangement , stereospecificity , diastereomer , chemistry , phosphine , borylation , salt (chemistry) , combinatorial chemistry , catalysis , ligand (biochemistry) , surface modification , boron , stereochemistry , organic chemistry , enantioselective synthesis , aryl , biochemistry , alkyl , receptor
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.