Catalytic C-H amination: the stereoselectivity issue
- PMID: 21234469
- DOI: 10.1039/c0cs00095g
Catalytic C-H amination: the stereoselectivity issue
Abstract
Catalytic C-H amination has recently emerged as a unique tool for the synthesis of amines. This tutorial review highlights the existing protocols catalyzed by metal complexes (rhodium, copper, ruthenium, manganese and palladium) allowing diastereo- and enantioselective C-H amination. Substrate-, catalyst- and reagent-controlled methodologies are detailed. They involve either catalytic nitrene C-H insertion or C-H activation.
Similar articles
-
De novo synthesis of Troc-protected amines: intermolecular rhodium-catalyzed C-H amination with N-tosyloxycarbamates.Org Lett. 2007 Feb 15;9(4):639-42. doi: 10.1021/ol062953t. Epub 2007 Jan 23. Org Lett. 2007. PMID: 17243710
-
Mechanistic Investigations of the AuCl3-Catalyzed Nitrene Insertion into an Aromatic C-H Bond of Mesitylene.J Org Chem. 2015 Jun 5;80(11):5795-803. doi: 10.1021/acs.joc.5b00764. Epub 2015 May 27. J Org Chem. 2015. PMID: 26014208
-
Toward a synthetically useful stereoselective C-H amination of hydrocarbons.J Am Chem Soc. 2008 Jan 9;130(1):343-50. doi: 10.1021/ja076519d. Epub 2007 Dec 12. J Am Chem Soc. 2008. PMID: 18072775
-
Catalytic C-H functionalization by metalloporphyrins: recent developments and future directions.Chem Soc Rev. 2011 Apr;40(4):1899-909. doi: 10.1039/c0cs00070a. Epub 2010 Nov 19. Chem Soc Rev. 2011. PMID: 21088785 Review.
-
Catalytic C-H amination: recent progress and future directions.Chem Commun (Camb). 2009 Sep 14;(34):5061-74. doi: 10.1039/b905820f. Epub 2009 Jul 7. Chem Commun (Camb). 2009. PMID: 20448953 Review.
Cited by
-
Iminoiodane- and Brønsted base-mediated cross dehydrogenative coupling of cyclic ethers with 1,3-dicarbonyl compounds.Molecules. 2015 Jul 22;20(7):13336-53. doi: 10.3390/molecules200713336. Molecules. 2015. PMID: 26205058 Free PMC article.
-
Silver-Catalyzed Enantioselective Propargylic C-H Bond Amination through Rational Ligand Design.J Am Chem Soc. 2020 Jul 29;142(30):12930-12936. doi: 10.1021/jacs.0c05726. Epub 2020 Jul 16. J Am Chem Soc. 2020. PMID: 32659081 Free PMC article.
-
Catalytic Enantioselective Allylic Amination of Olefins for the Synthesis of ent-Sitagliptin.Synlett. 2013 Nov 1;24(18):2459-2463. doi: 10.1055/s-0033-1340079. Synlett. 2013. PMID: 25378809 Free PMC article.
-
Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation.J Am Chem Soc. 2021 Jul 14;143(27):10070-10076. doi: 10.1021/jacs.1c05206. Epub 2021 Jun 28. J Am Chem Soc. 2021. PMID: 34181401 Free PMC article.
-
Intramolecular 1,5-C(sp3)-H Radical Amination via Co(II)-Based Metalloradical Catalysis for Five-Membered Cyclic Sulfamides.Chem Sci. 2016;7(12):6934-6939. doi: 10.1039/C6SC02231F. Epub 2016 Jul 28. Chem Sci. 2016. PMID: 28138382 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources