Stereospecific synthesis of α-hydroxy-cyclopropylboronates from allylic epoxides
Entity
UAM. Departamento de Química OrgánicaPublisher
WileyDate
2019-01-02Citation
10.1002/anie.201812836
Angewandte Chemie - International Edition 58.10 (2019): 3188-3192
ISSN
1433-7851 (print); 1521-3773 (online)DOI
10.1002/anie.201812836Funded by
We thank the European Research Council (ERC-337776) and MINECO (CTQ2016-78779-R) for financial supportProject
info:eu-repo/grantAgreement/EC/FP7/337776; Gobierno de España. CTQ2016-78779-REditor's Version
https://doi.org/10.1002/anie.201812836Subjects
allylic epoxide; boron; copper; cyclopropane; cyclopropylboronate; QuímicaNote
This is the peer reviewed version of the following article: Angewandte Chemie - International Edition 58.10 (2019): 3188-03192, which has been published in final form at https://doi.org/10.1002/anie.201812836. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived VersionsRights
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim HereinAbstract
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
Files in this item
Google Scholar:Amenós, Laura
-
Trulli, Laura
-
Nóvoa, Luis
-
Parra, Alejandro
-
Tortosa Manzanares, Mariola
This item appears in the following Collection(s)
Related items
Showing items related by title, author, creator and subject.