Stereospecific Synthesis of α-Hydroxy-Cyclopropylboronates from Allylic Epoxides
Laura Amenós
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorDr. Laura Trulli
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorLuis Nóvoa
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorDr. Alejandro Parra
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorCorresponding Author
Dr. Mariola Tortosa
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorLaura Amenós
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorDr. Laura Trulli
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorLuis Nóvoa
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorDr. Alejandro Parra
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorCorresponding Author
Dr. Mariola Tortosa
Organic Chemistry Department, Institute for Advance Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain
Search for more papers by this authorGraphical Abstract
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 CuI 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.
Supporting Information
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