C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands: their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines
- PMID: 15493893
- DOI: 10.1021/ja044790e
C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands: their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines
Abstract
Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99% ee) was realized by use of a new C2-symmetric diene ligand, (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod*), for the rhodium-catalyzed asymmetric arylation of N-tosylarylimines with arylboroxines.
Similar articles
-
C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines.Org Lett. 2005 Jan 20;7(2):307-10. doi: 10.1021/ol0476063. Org Lett. 2005. PMID: 15646984
-
Asymmetric addition of dimethylzinc to N-tosylarylimines catalyzed by a rhodium-diene complex toward the synthesis of chiral 1-arylethylamines.Org Lett. 2006 Mar 2;8(5):979-81. doi: 10.1021/ol060213e. Org Lett. 2006. PMID: 16494489
-
Preparation of C2-symmetric bicyclo[2.2.2]octa-2,5-diene ligands and their use for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids.J Org Chem. 2005 Apr 1;70(7):2503-8. doi: 10.1021/jo047831y. J Org Chem. 2005. PMID: 15787536
-
C1-symmetric dicyclopentadienes as new chiral diene ligands for asymmetric rhodium-catalyzed arylation of N-tosylarylimines.Org Lett. 2010 Sep 3;12(17):3820-3. doi: 10.1021/ol101531r. Org Lett. 2010. PMID: 20704187
-
Asymmetric hydrogenation using monodentate phosphoramidite ligands.Acc Chem Res. 2007 Dec;40(12):1267-77. doi: 10.1021/ar7001107. Epub 2007 Aug 18. Acc Chem Res. 2007. PMID: 17705446 Review.
Cited by
-
The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions.Chem Sci. 2015 Dec 1;6(12):7163-7168. doi: 10.1039/c5sc02100f. Epub 2015 Sep 14. Chem Sci. 2015. PMID: 29861953 Free PMC article.
-
An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones.Molecules. 2012 Dec 20;18(1):14-26. doi: 10.3390/molecules18010014. Molecules. 2012. PMID: 23344185 Free PMC article.
-
Nickel-catalyzed enantioselective vinylation of aryl 2-azaallyl anions.Chem Sci. 2021 Mar 26;12(18):6406-6412. doi: 10.1039/d1sc00972a. Chem Sci. 2021. PMID: 34084440 Free PMC article.
-
Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.J Org Chem. 2017 Nov 3;82(21):11326-11336. doi: 10.1021/acs.joc.7b02339. J Org Chem. 2017. PMID: 29020446 Free PMC article.
-
Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions.Org Lett. 2008 Oct 2;10(19):4387-9. doi: 10.1021/ol801931v. Epub 2008 Sep 5. Org Lett. 2008. PMID: 18771267 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous