doi: 10.1021/jo101004x.
Lewis acid catalyzed highly stereoselective domino-ring-opening cyclization of activated aziridines with enolates: synthesis of functionalized chiral γ-lactams
Affiliations
- PMID: 20707384
- DOI: 10.1021/jo101004x
Item in Clipboard
Lewis acid catalyzed highly stereoselective domino-ring-opening cyclization of activated aziridines with enolates: synthesis of functionalized chiral γ-lactams
J Org Chem.
.
Abstract
A highly enantio- and diastereoselective Lewis acid catalyzed S(N)2-type ring opening followed by cyclization of aziridines with active methylene carbon nucleophiles to functionalized chiral γ-lactams in a domino fashion has been developed. γ-Lactams have been desulfonated and decarboxylated, providing pyrrolidone-3-carboxylate and N-tosylpyrrolidinone derivatives, respectively, in good yields.
Similar articles
-
Ring opening/C-N cyclization of activated aziridines with carbon nucleophiles: highly diastereo- and enantioselective synthesis of tetrahydroquinolines.Org Lett. 2011 Aug 19;13(16):4256-9. doi: 10.1021/ol2016077. Epub 2011 Jul 18. Org Lett. 2011. PMID: 21766866
-
Synthetic route to chiral tetrahydroquinoxalines via ring-opening of activated aziridines.Org Lett. 2011 Nov 18;13(22):5972-5. doi: 10.1021/ol2023906. Epub 2011 Oct 17. Org Lett. 2011. PMID: 22004011
-
Highly efficient copper-catalyzed domino ring opening and Goldberg coupling cyclization for the synthesis of 3,4-dihydro-2H-1,4-benzoxazines.Org Lett. 2009 May 7;11(9):1923-6. doi: 10.1021/ol9003299. Org Lett. 2009. PMID: 19341265
-
Recent developments in the use of catalytic asymmetric ammonium enolates in chemical synthesis.Chem Rev. 2007 Dec;107(12):5596-605. doi: 10.1021/cr0683764. Chem Rev. 2007. PMID: 18072805 Review. No abstract available.
-
Chiral dialkylaminopyridine catalysts in asymmetric synthesis.Chem Rev. 2007 Dec;107(12):5570-95. doi: 10.1021/cr068370e. Chem Rev. 2007. PMID: 18072804 Review. No abstract available.
Cited by
-
N-Heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis.Beilstein J Org Chem. 2012;8:398-402. doi: 10.3762/bjoc.8.43. Epub 2012 Mar 14. Beilstein J Org Chem. 2012. PMID: 22509208 Free PMC article.
-
Asymmetric Catalytic Access to Piperazin-2-ones and Morpholin-2-ones in a One-Pot Approach: Rapid Synthesis of an Intermediate to Aprepitant.J Org Chem. 2023 Jun 16;88(12):7888-7892. doi: 10.1021/acs.joc.2c02491. Epub 2023 Feb 21. J Org Chem. 2023. PMID: 36808952 Free PMC article.
-
α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams.Beilstein J Org Chem. 2021 Mar 9;17:688-704. doi: 10.3762/bjoc.17.58. eCollection 2021. Beilstein J Org Chem. 2021. PMID: 33777244 Free PMC article.
-
Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck-Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles.Beilstein J Org Chem. 2024 Apr 29;20:940-949. doi: 10.3762/bjoc.20.84. eCollection 2024. Beilstein J Org Chem. 2024. PMID: 38711594 Free PMC article.
-
Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with β-Keto Esters.European J Org Chem. 2020 Aug 31;2020(32):5173-5177. doi: 10.1002/ejoc.202000916. Epub 2020 Jul 15. European J Org Chem. 2020. PMID: 32982577 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
