Stereospecific Synthesis of α-Hydroxy-Cyclopropylboronates from Allylic Epoxides.
allylic epoxide
boron
copper
cyclopropane
cyclopropylboronate
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
04 03 2019
04 03 2019
Historique:
received:
08
11
2018
revised:
20
12
2018
pubmed:
3
1
2019
medline:
3
1
2019
entrez:
3
1
2019
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 30600867
doi: 10.1002/anie.201812836
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
3188-3192Subventions
Organisme : FP7 Ideas: European Research Council
ID : 337776
Pays : International
Organisme : Secretaría de Estado de Investigación, Desarrollo e Innovación
ID : CTQ2016-78779-R
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.