doi: 10.1021/acs.joc.5b00055.
Epub 2015 Jan 29.
Lewis acid template-catalyzed asymmetric diels-alder reaction
Affiliations
- PMID: 25621816
- DOI: 10.1021/acs.joc.5b00055
Item in Clipboard
Lewis acid template-catalyzed asymmetric diels-alder reaction
J Org Chem.
.
Abstract
An asymmetric Diels-Alder reaction of 2,4-dienols and methyl acrylate utilizing a chiral Zn(II)/Mg(II) bimetallic template with low catalyst loading was successfully achieved. The bimetallic Lewis acid template derived from (R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol catalyzed the Diels-Alder reaction in the presence of molecular sieves 4 Å to afford various functionalized bicyclic γ-lactones with high enantiomeric purities.
Similar articles
-
Enantioselective total synthesis of (-)-dactylolide.Org Lett. 2006 Mar 16;8(6):1117-20. doi: 10.1021/ol053092b. Org Lett. 2006. PMID: 16524282
-
Oxidative radical cyclisations for the synthesis of gamma-lactones.Chem Commun (Camb). 2008 Jun 14;(22):2559-61. doi: 10.1039/b802473a. Epub 2008 Apr 21. Chem Commun (Camb). 2008. PMID: 18506243
-
Lewis acid-Lewis base catalyzed enantioselective hetero-Diels-Alder reaction for direct access to delta-lactones.Org Lett. 2008 May 15;10(10):2019-22. doi: 10.1021/ol800742d. Epub 2008 Apr 23. Org Lett. 2008. PMID: 18429619
-
Synthetic, semisynthetic and natural analogues of peloruside A.Chem Commun (Camb). 2015 Mar 21;51(23):4750-65. doi: 10.1039/c4cc09785h. Chem Commun (Camb). 2015. PMID: 25642465 Review.
-
Domino reactions for the synthesis of bridged bicyclic frameworks: fast access to bicyclo[n.3.1]alkanes.Chem Soc Rev. 2011 Jul;40(7):3445-54. doi: 10.1039/c1cs15018a. Epub 2011 Apr 11. Chem Soc Rev. 2011. PMID: 21483949 Review.
Cited by
-
Enantiodivergent [4+2] Cycloaddition of Dienolates by Polyfunctional Lewis Acid/Zwitterion Catalysis.Angew Chem Int Ed Engl. 2020 Nov 2;59(45):19873-19877. doi: 10.1002/anie.202009093. Epub 2020 Aug 28. Angew Chem Int Ed Engl. 2020. PMID: 32697020 Free PMC article.
-
Collective Total Synthesis of Four Ganoderma Meroterpenoids Based on an Intramolecular Aldol Strategy.Org Lett. 2025 Mar 7;27(9):2049-2052. doi: 10.1021/acs.orglett.4c04756. Epub 2025 Feb 24. Org Lett. 2025. PMID: 39994830 Free PMC article.
-
Combining iminium and supramolecular catalysis for the [4 + 2] cycloaddition of E-cinnamaldehydes.Org Biomol Chem. 2022 Aug 24;20(33):6646-6653. doi: 10.1039/d2ob01171a. Org Biomol Chem. 2022. PMID: 35938223 Free PMC article.
-
Progress in Lewis-Acid-Templated Diels-Alder Reactions.Molecules. 2024 Mar 6;29(5):1187. doi: 10.3390/molecules29051187. Molecules. 2024. PMID: 38474699 Free PMC article. Review.
-
Oxidative generation of isobenzofurans from phthalans: application to the formal synthesis of (±)-morphine.Chem Sci. 2024 Oct 19;15(45):19070-6. doi: 10.1039/d4sc05890a. Online ahead of print. Chem Sci. 2024. PMID: 39483252 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
