Highly diastereoselective preparation of chiral NHC-boranes stereogenic at the boron atom.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
14 Jul 2019
14 Jul 2019
Historique:
received:
25
03
2019
accepted:
23
05
2019
entrez:
26
7
2019
pubmed:
26
7
2019
medline:
26
7
2019
Statut:
epublish
Résumé
Stereogenic main group elements are clearly generating interest in the enantioselective catalysis field. Surprisingly, while chiral organoboron reagents are very useful in stereoselective transformations, few scaffolds stereogenic at boron and configurationally stable have been reported to date. Herein, we describe an original library of chiral NHC-boranes, stereogenic at the boron atom, that has been prepared in only a few steps and in good yields (up to 93%). Key steps involve a chlorination/arylation sequence in the presence of simple Grignard reagents from bicyclic NHC-boranes. The high and unprecedented diastereoselectivity observed during the second step (up to 99 : 1 dr) has been rationalized through a plausible S
Identifiants
pubmed: 31341605
doi: 10.1039/c9sc01454c
pii: c9sc01454c
pmc: PMC6611065
doi:
Types de publication
Journal Article
Langues
eng
Pagination
6524-6530Références
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