Synthesis of chiral boranes asymmetric insertion of carbenes into B-H bonds catalyzed by the rhodium() 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 in:Chemical communications (Cambridge, England) England), 2024-08, Vol.6 (65), p.861-864
Main Authors: Ankudinov, Nikita M, Komarova, Alina A, Podyacheva, Evgeniya S, Chusov, Denis A, Danshina, Anastasia A, Perekalin, Dmitry S
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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. Catalytic insertion of diazo compounds into B-H bonds produces unique compounds with tetrahedral chiral boron atoms.
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc02969k