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 in | Chemical communications (Cambridge, England) Vol. 60; no. 65; pp. 8601 - 8604 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
09.08.2024
Royal Society of Chemistry |
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| Abstract | 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. |
|---|---|
| AbstractList | 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-BH2R. The reaction is catalyzed by the rhodium(I) complex with the chiral diene ligand tBu2-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.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-BH2R. The reaction is catalyzed by the rhodium(I) complex with the chiral diene ligand tBu2-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. Molecules with chiral boron atoms have been scarcely studied due to limited synthetic access. Herein, we report a new method for their synthesis asymmetric insertion of arydiazoacetates into the B-H bonds of prochiral carbene-boranes NHC-BH R. The reaction is catalyzed by the rhodium(I) complex with the chiral diene ligand Bu -TFB, which can be conveniently prepared by diastereoselective coordination of the racemic diene with ( -Salox)Rh(CO) . The target boranes were typically obtained in 75-90% yields with 90-95% ee. 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-BH2R. The reaction is catalyzed by the rhodium(I) complex with the chiral diene ligand Bu-t(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. 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. 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–BH2R. The reaction is catalyzed by the rhodium(i) complex with the chiral diene ligand tBu2-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. |
| Author | Podyacheva, Evgeniya S. Chusov, Denis A. Komarova, Alina A. Ankudinov, Nikita M. Danshina, Anastasia A. Perekalin, Dmitry S. |
| Author_xml | – sequence: 1 givenname: Nikita M. orcidid: 0000-0003-3476-3789 surname: Ankudinov fullname: Ankudinov, Nikita M. organization: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119334, Moscow, Russia – sequence: 2 givenname: Alina A. surname: Komarova fullname: Komarova, Alina A. organization: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119334, Moscow, Russia – sequence: 3 givenname: Evgeniya S. surname: Podyacheva fullname: Podyacheva, Evgeniya S. organization: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119334, Moscow, Russia, National Research University Higher School of Economics, 7 Vavilova str., 117312, Moscow, Russia – sequence: 4 givenname: Denis A. orcidid: 0000-0001-6770-5484 surname: Chusov fullname: Chusov, Denis A. organization: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119334, Moscow, Russia, National Research University Higher School of Economics, 7 Vavilova str., 117312, Moscow, Russia – sequence: 5 givenname: Anastasia A. surname: Danshina fullname: Danshina, Anastasia A. organization: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russia – sequence: 6 givenname: Dmitry S. orcidid: 0000-0002-0864-8907 surname: Perekalin fullname: Perekalin, Dmitry S. organization: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119334, Moscow, Russia, National Research University Higher School of Economics, 7 Vavilova str., 117312, Moscow, Russia |
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| Snippet | 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... 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... Molecules with chiral boron atoms have been scarcely studied due to limited synthetic access. Herein, we report a new method for their synthesis asymmetric... |
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| SubjectTerms | Asymmetry Boranes Carbenes Chemical bonds Chemical synthesis Chemistry Chemistry, Multidisciplinary Insertion Physical Sciences Rhodium Science & Technology Stereoselectivity |
| Title | Synthesis of chiral boranes via asymmetric insertion of carbenes into B–H bonds catalyzed by the rhodium( i ) diene complex |
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