2-(1-炔基)-2-烯-1-酮与硝酮的非对映和对映选择性金(I)催化分子间串联环化/[3+3]环加成反应 - Suppr

Diastereo- and enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3+3]cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with nitrones.

作者信息

Liu Feng, Qian Deyun, Li Lei, Zhao Xiaoli, Zhang Junliang

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, PR China.

出版信息

Angew Chem Int Ed Engl. 2010 Sep 3;49(37):6669-72. doi: 10.1002/anie.201003136.

DOI:10.1002/anie.201003136

PMID:20669211

Abstract

摘要

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Diastereo- and enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3+3]cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with nitrones.

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Diastereo- and enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3+3]cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with nitrones.

作者信息

Liu Feng, Qian Deyun, Li Lei, Zhao Xiaoli, Zhang Junliang

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, PR China.

出版信息

Angew Chem Int Ed Engl. 2010 Sep 3;49(37):6669-72. doi: 10.1002/anie.201003136.

DOI:10.1002/anie.201003136

PMID:20669211

Abstract

摘要

相似文献

Diastereo- and enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3+3]cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with nitrones.

Angew Chem Int Ed Engl. 2010 Sep 3;49(37):6669-72. doi: 10.1002/anie.201003136.

Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Cyclization-[4+3] Annulation Cascades between 2-(1-Alkynyl)-2-alken-1-ones and Anthranils.

Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10396-10400. doi: 10.1002/anie.202001854. Epub 2020 Apr 15.

Highly substituted furo[3,4-d][1,2]oxazines: gold-catalyzed regiospecific and diastereoselective 1,3-dipolar cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with nitrones.

Angew Chem Int Ed Engl. 2009;48(30):5505-8. doi: 10.1002/anie.200901299.

Ming-Phos/Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of Indolyl-Substituted Cyclopenta[ c]furans.

Org Lett. 2018 Oct 19;20(20):6403-6406. doi: 10.1021/acs.orglett.8b02701. Epub 2018 Oct 1.

Highly Regio-, Diastereo-, and Enantioselective Gold(I)-Catalyzed Intermolecular Annulations with N-Allenamides at the Proximal C=C Bond.

Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14849-52. doi: 10.1002/anie.201507165. Epub 2015 Sep 22.

Furans versus 4H-pyrans: catalyst-controlled regiodivergent tandem Michael addition-cyclization reaction of 2-(1-alkynyl)-2-alken-1-ones with 1,3-dicarbonyl compounds.

Chem Commun (Camb). 2009 Jun 28(24):3594-6. doi: 10.1039/b905267d. Epub 2009 May 11.

Furan-based o-quinodimethanes by gold-catalyzed dehydrogenative heterocyclization of 2-(1-alkynyl)-2-alken-1-ones: a modular entry to 2,3-furan-fused carbocycles.

Angew Chem Int Ed Engl. 2014 Jun 16;53(25):6542-5. doi: 10.1002/anie.201403709. Epub 2014 May 18.

Synthesis of 2-acylfurans from 3-(1-alkynyl)-2-alken-1-ones via the oxidation of gold-carbene intermediates by H2O2.

Dalton Trans. 2010 May 14;39(18):4270-3. doi: 10.1039/c0dt00024h.

Enantioselective Gold(I)-Catalyzed Heterocyclization-Intermolecular Exo [4 + 3]-Cycloaddition Reactions for the Synthesis of Chiral Oxa-Bridged Benzocycloheptanes.

Org Lett. 2019 May 3;21(9):3018-3022. doi: 10.1021/acs.orglett.9b00537. Epub 2019 Apr 17.

AuCl(3)-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones.

J Am Chem Soc. 2004 Sep 15;126(36):11164-5. doi: 10.1021/ja0466964.

引用本文的文献

Recent Advancements in the Cyclization Strategies of 1,3-Enynes Towards the Synthesis of Heterocyclic/Carbocyclic Frameworks.

Chem Asian J. 2025 Apr 17;20(8):e202401657. doi: 10.1002/asia.202401657. Epub 2025 Mar 4.

Catalytic [4+2]- and [4+4]-cycloaddition using furan-fused cyclobutanone as a privileged C4 synthon.

Nat Commun. 2024 Jun 26;15(1):5407. doi: 10.1038/s41467-024-49664-5.

Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors.

Commun Chem. 2023 Jun 19;6(1):128. doi: 10.1038/s42004-023-00921-6.

H-Bonded Counterion-Directed Catalysis: Enantioselective Gold(I)-Catalyzed Addition to 2-Alkynyl Enones as a Case Study.

European J Org Chem. 2022 Oct 13;2022(38):e202200518. doi: 10.1002/ejoc.202200518. Epub 2022 Jul 13.

Indium-Catalysed Transfer Hydrogenation for the Reductive Cyclisation of 2-Alkynyl Enones towards Trisubstituted Furans.

Angew Chem Int Ed Engl. 2021 Oct 25;60(44):23661-23666. doi: 10.1002/anie.202109266. Epub 2021 Oct 1.

Enantioselective gold-catalyzed intermolecular [2+2] [4+2]-cycloadditions of 3-styrylindoles with -allenamides: observation of interesting substituent effects.

Chem Sci. 2015 Oct 1;6(10):5564-5570. doi: 10.1039/c5sc01827g. Epub 2015 Jun 23.

Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans.

Chem Sci. 2015 Jul 1;6(7):4242-4246. doi: 10.1039/c5sc01052g. Epub 2015 Apr 27.

Diastereoselective Synthesis of Cyclopenta[c]furans by a Catalytic Multicomponent Reaction.

Angew Chem Int Ed Engl. 2016 Sep 19;55(39):11863-6. doi: 10.1002/anie.201606108. Epub 2016 Aug 19.

Atropisomeric [(diphosphine)Au2 Cl2 ] complexes and their catalytic activity towards asymmetric cycloisomerisation of 1,6-enynes.

Chemistry. 2015 Feb 2;21(6):2686-90. doi: 10.1002/chem.201404496. Epub 2014 Dec 11.

Gold(I)-catalyzed enantioselective cycloaddition reactions.

Beilstein J Org Chem. 2013 Oct 30;9:2250-64. doi: 10.3762/bjoc.9.264.

Diastereo- and enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3+3]cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with nitrones.

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Diastereo- and enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3+3]cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with nitrones.

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