Guanidine-Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates.
asymmetric catalysis
borylation
copper
enantioconvergent synthesis
guanidines
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:
18 02 2019
18 02 2019
Historique:
received:
27
11
2018
revised:
05
01
2019
pubmed:
8
1
2019
medline:
8
1
2019
entrez:
8
1
2019
Statut:
ppublish
Résumé
An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine-copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed into diverse functionalized allylic compounds without erosion of optical purity. Experimental and DFT mechanistic studies support an S
Identifiants
pubmed: 30615241
doi: 10.1002/anie.201813490
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2382-2386Subventions
Organisme : Nanyang Technological University
ID : M4011633
Pays : International
Organisme : Ministry of Education Singapore
ID : MOE2016-T2-1-087
Pays : International
Organisme : Singapore University of Technology and Design
ID : T1MOE1706 & IDG31800104
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.