Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives
- PMID: 16836413
- DOI: 10.1021/ol061389j
Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives
Abstract
[Structure: see text] Under special conditions, N-phthaloyl-alpha-amino acid amides of 8-aminoquinoline can be either acetoxylated or arylated selectively at the beta-carbon. In certain cases, arylation can be effected at the gamma-carbon.
Similar articles
-
Three-component synthesis of alpha,beta-cyclopropyl-gamma-amino acids.Org Lett. 2005 Mar 17;7(6):1137-40. doi: 10.1021/ol0501525. Org Lett. 2005. PMID: 15760158
-
Preparation of photoactivable amino acid derivatives.J Org Chem. 2009 Jun 19;74(12):4519-24. doi: 10.1021/jo900442p. J Org Chem. 2009. PMID: 19476329
-
Novel syntheses of chiral beta- and gamma-amino acid derivatives utilizing N-protected (aminoacyl)benzotriazoles from aspartic and glutamic acids.J Org Chem. 2007 Jan 19;72(2):407-14. doi: 10.1021/jo061667s. J Org Chem. 2007. PMID: 17221955
-
The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.Chem Biodivers. 2004 Aug;1(8):1111-239. doi: 10.1002/cbdv.200490087. Chem Biodivers. 2004. PMID: 17191902 Review.
-
Synthesis and applications of silicon-containing alpha-amino acids.Chem Soc Rev. 2009 Apr;38(4):1002-10. doi: 10.1039/b816769a. Epub 2009 Feb 16. Chem Soc Rev. 2009. PMID: 19421578 Review.
Cited by
-
Stereoselective alkoxycarbonylation of unactivated C(sp3)-H bonds with alkyl chloroformates via Pd(II)/Pd(IV) catalysis.Nat Commun. 2016 Sep 28;7:12901. doi: 10.1038/ncomms12901. Nat Commun. 2016. PMID: 27678161 Free PMC article.
-
Controlling site selectivity in palladium-catalyzed C-H bond functionalization.Acc Chem Res. 2012 Jun 19;45(6):936-46. doi: 10.1021/ar300014f. Epub 2012 May 3. Acc Chem Res. 2012. PMID: 22554114 Free PMC article.
-
Multiple remote C(sp3)-H functionalizations of aliphatic ketones via bimetallic Cu-Pd catalyzed successive dehydrogenation.Chem Sci. 2022 Nov 14;13(46):13843-13850. doi: 10.1039/d2sc05370e. eCollection 2022 Nov 30. Chem Sci. 2022. PMID: 36544736 Free PMC article.
-
Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.Chem Rev. 2021 Dec 22;121(24):14957-15074. doi: 10.1021/acs.chemrev.1c00519. Epub 2021 Oct 29. Chem Rev. 2021. PMID: 34714620 Free PMC article. Review.
-
Copper-catalyzed etherification of arene C-H bonds.Org Lett. 2013 Nov 15;15(22):5842-5. doi: 10.1021/ol402904d. Epub 2013 Nov 1. Org Lett. 2013. PMID: 24180517 Free PMC article.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources