doi: 10.1039/c7cs00386b.
A continuing challenge: N-heterocyclic carbene-catalyzed syntheses of γ-butyrolactones
Affiliations
- PMID: 29372207
- DOI: 10.1039/c7cs00386b
Item in Clipboard
A continuing challenge: N-heterocyclic carbene-catalyzed syntheses of γ-butyrolactones
Chem Soc Rev.
.
Abstract
Catalytic, stereoselective N-heterocyclic carbene-catalyzed reactions facilitate efficient construction of many different heterocyclic compounds, such as the enantioenriched 5-membered (γ) lactones highlighted in this tutorial review. Herein, various strategies to enable formal [3+2] type annulations between electrophilic carbonyl equivalents and homoenolate nucleophiles for the synthesis of γ-lactones are summarized.
Similar articles
-
N-heterocyclic carbene-catalyzed generation of homoenolates: gamma-butyrolactones by direct annulations of enals and aldehydes.J Am Chem Soc. 2004 Nov 10;126(44):14370-1. doi: 10.1021/ja044714b. J Am Chem Soc. 2004. PMID: 15521753
-
Recent advances in carbon-carbon bond-forming reactions involving homoenolates generated by NHC catalysis.Chem Soc Rev. 2008 Dec;37(12):2691-8. doi: 10.1039/b719083m. Epub 2008 Oct 21. Chem Soc Rev. 2008. PMID: 19020682
-
Enantioselective synthesis of spiro γ-butyrolactones by N-heterocyclic carbene (NHC)-catalyzed formal [3 + 2] annulation of enals with 3-hydroxy oxindoles.Org Biomol Chem. 2017 Mar 1;15(9):2013-2019. doi: 10.1039/c7ob00148g. Org Biomol Chem. 2017. PMID: 28198907
-
N-Heterocyclic Carbene Catalyzed (5+1) Annulations Exploiting a Vinyl Dianion Synthon Strategy.Angew Chem Int Ed Engl. 2019 Aug 12;58(33):11483-11490. doi: 10.1002/anie.201905475. Epub 2019 Jul 8. Angew Chem Int Ed Engl. 2019. PMID: 31197900 Review.
-
Recent advances in employing homoenolates generated by N-heterocyclic carbene (NHC) catalysis in carbon-carbon bond-forming reactions.Chem Soc Rev. 2015 Aug 7;44(15):5040-52. doi: 10.1039/c5cs00162e. Epub 2015 May 27. Chem Soc Rev. 2015. PMID: 26014054 Review.
Cited by
-
An Electrochemical Way to Generate Amphiphiles from Hydrazones for the Synthesis of 1,2,4-Triazole Scaffold Cyclic Compounds.ChemistryOpen. 2022 Jan;11(1):e202100268. doi: 10.1002/open.202100268. ChemistryOpen. 2022. PMID: 35083886 Free PMC article.
-
Synergistic Copper-Aminocatalysis for Direct Tertiary α-Alkylation of Ketones with Electron-Deficient Alkanes.Adv Sci (Weinh). 2024 Aug;11(31):e2402255. doi: 10.1002/advs.202402255. Epub 2024 Jun 17. Adv Sci (Weinh). 2024. PMID: 38885363 Free PMC article.
-
NHC-catalyzed enantioselective access to β-cyano carboxylic esters via in situ substrate alternation and release.Nat Commun. 2023 Aug 12;14(1):4878. doi: 10.1038/s41467-023-40645-8. Nat Commun. 2023. PMID: 37573355 Free PMC article.
-
Carbene organic catalytic planar enantioselective macrolactonization.Nat Commun. 2024 Feb 1;15(1):958. doi: 10.1038/s41467-024-45218-x. Nat Commun. 2024. PMID: 38302464 Free PMC article.
-
Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides.Nat Commun. 2022 Aug 15;13(1):4793. doi: 10.1038/s41467-022-32428-4. Nat Commun. 2022. PMID: 35970848 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
