doi: 10.1039/c6ob01119e.
Epub 2016 Jun 23.
Catalytic asymmetric reactions and synthesis of quinones
Affiliations
- PMID: 27337246
- DOI: 10.1039/c6ob01119e
Item in Clipboard
Catalytic asymmetric reactions and synthesis of quinones
Org Biomol Chem.
.
Abstract
Asymmetric reactions and the synthesis of various quinones, carried out in the presence of chiral organocatalysts and metal-ligand complexes, are reviewed here. The role of quinones as Michael donors/acceptors, Diels-Alder dienophiles and 1,3-dipolarophiles has been extensively investigated to access complex structural frameworks. Additionally, reports in the literature on the stereoselective synthesis of simple and complex quinoidal compounds with potential biological activities have also been summarized in this review.
Similar articles
-
Aminocatalytic asymmetric Diels-Alder reactions via HOMO activation.Acc Chem Res. 2012 Sep 18;45(9):1491-500. doi: 10.1021/ar3000822. Epub 2012 Jun 20. Acc Chem Res. 2012. PMID: 22716926
-
(1R)-(+)-camphor and acetone derived alpha'-hydroxy enones in asymmetric Diels-Alder reaction: catalytic activation by Lewis and Brønsted acids, substrate scope, applications in syntheses, and mechanistic studies.J Org Chem. 2010 Mar 5;75(5):1458-73. doi: 10.1021/jo9023039. J Org Chem. 2010. PMID: 20121243
-
Quinones as dienophiles in the Diels-Alder reaction: history and applications in total synthesis.Angew Chem Int Ed Engl. 2014 Feb 17;53(8):2056-77. doi: 10.1002/anie.201305908. Epub 2014 Jan 20. Angew Chem Int Ed Engl. 2014. PMID: 24446164
-
DNA-based hybrid catalysts for asymmetric organic synthesis.Angew Chem Int Ed Engl. 2010 May 25;49(23):3870-8. doi: 10.1002/anie.200905382. Angew Chem Int Ed Engl. 2010. PMID: 20455226 Review.
-
Artificial metalloenzymes as catalysts in stereoselective Diels-Alder reactions.Chem Rec. 2012 Aug;12(4):391-406. doi: 10.1002/tcr.201100043. Epub 2012 Jun 18. Chem Rec. 2012. PMID: 22711577 Review.
Cited by
-
Oxidative radical coupling of hydroquinones and thiols using chromic acid: one-pot synthesis of quinonyl alkyl/aryl thioethers.RSC Adv. 2020 May 21;10(33):19454-19462. doi: 10.1039/d0ra01519a. eCollection 2020 May 20. RSC Adv. 2020. PMID: 35515459 Free PMC article.
-
Encapsulation of nor-β-lapachone into poly(d,l)-lactide-co-glycolide (PLGA) microcapsules: full characterization, computational details and cytotoxic activity against human cancer cell lines.Medchemcomm. 2017 Sep 7;8(10):1993-2002. doi: 10.1039/c7md00196g. eCollection 2017 Oct 1. Medchemcomm. 2017. PMID: 30108718 Free PMC article.
-
2-Amino-1,4-naphthoquinone as a key precursor for naphthoquinone-fused N-heterocycles: synthetic approaches and mechanistic perspectives.Mol Divers. 2025 May 14. doi: 10.1007/s11030-025-11201-x. Online ahead of print. Mol Divers. 2025. PMID: 40366551 Review.
-
Benzoquinone Enhances Hyperpolarization of Surface Alcohols with Para-Hydrogen.J Am Chem Soc. 2023 May 10;145(18):9970-9975. doi: 10.1021/jacs.3c01593. Epub 2023 Apr 26. J Am Chem Soc. 2023. PMID: 37127286 Free PMC article.
-
A fast and responsive turn-on fluorescent probe based on a quinone conjugated alkoxy derivative for biothiols and a cellular imaging study.Turk J Chem. 2024 Nov 11;48(6):830-842. doi: 10.55730/1300-0527.3702. eCollection 2024. Turk J Chem. 2024. PMID: 39780844 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
