Synthesis of chiral boranes via asymmetric insertion of carbenes into B–H bonds catalyzed by the rhodium( i ) diene complex

Molecules with chiral boron atoms have been scarcely studied due to limited synthetic access. Herein, we report a new method for their synthesis via asymmetric insertion of arydiazoacetates into the B–H bonds of prochiral carbene–boranes NHC–BH 2 R. The reaction is catalyzed by the rhodium( i ) comp...

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Published inChemical communications (Cambridge, England) Vol. 60; no. 65; pp. 8601 - 8604
Main Authors Ankudinov, Nikita M., Komarova, Alina A., Podyacheva, Evgeniya S., Chusov, Denis A., Danshina, Anastasia A., Perekalin, Dmitry S.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 09.08.2024
Royal Society of Chemistry
Subjects
Asymmetry
Boranes
Carbenes
Chemical bonds
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Insertion
Physical Sciences
Rhodium
Science & Technology
Stereoselectivity
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Summary:Molecules with chiral boron atoms have been scarcely studied due to limited synthetic access. Herein, we report a new method for their synthesis via asymmetric insertion of arydiazoacetates into the B–H bonds of prochiral carbene–boranes NHC–BH 2 R. The reaction is catalyzed by the rhodium( i ) complex with the chiral diene ligand t Bu 2 -TFB, which can be conveniently prepared by diastereoselective coordination of the racemic diene with ( S -Salox)Rh(CO) 2 . The target boranes were typically obtained in 75–90% yields with 90–95% ee.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/D4CC02969K