A New Route to Silyl-substituted Cyclobutenones and Silylketenes.
作者信息
Benda Konstantin, Knoth Tanja, Danheiser Rick L, Schaumann Ernst
机构信息
Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstraβe 6, 38678 Clausthal-Zellerfeld, Germany.
出版信息
Tetrahedron Lett. 2011 Jan 5;52(1):46-48. doi: 10.1016/j.tetlet.2010.10.130.
Abstract
2-Silyl-cyclobutene(di)ones are obtained by an addition/substitution approach on dimethyl squarate using silyl anions. The acetal and in particular the thioacetal derivatives readily undergo electrocyclic ring opening to reactive silyl(vinyl)ketenes.
摘要
相似文献
1
A New Route to Silyl-substituted Cyclobutenones and Silylketenes.
Tetrahedron Lett. 2011 Jan 5;52(1):46-48. doi: 10.1016/j.tetlet.2010.10.130.
2
A Silyl Substituent Can Dictate a Concerted Electrocyclic Pathway: Inward Torquoselectivity in the Ring Opening of 3-Silyl-1-cyclobutene.
Angew Chem Int Ed Engl. 2001 Jan 5;40(1):189-190.
3
Lewis Acid-Activated Reactions of Silyl Ketenes for the Preparation of α-Silyl Carbonyl Compounds.
J Org Chem. 2019 Nov 15;84(22):14461-14468. doi: 10.1021/acs.joc.9b01859. Epub 2019 Nov 5.
4
Effect of Remote Substituents on the Torquoselectivity of 3-Silyl Cyclobutene-Derivatives Ring-Opening Reactions.
Chemphyschem. 2020 Aug 18;21(16):1805-1813. doi: 10.1002/cphc.202000451. Epub 2020 Jul 21.
5
Synthesis of highly substituted allenylsilanes by alkylidenation of silylketenes.
Beilstein J Org Chem. 2005 Aug 26;1(1):5. doi: 10.1186/1860-5397-1-5.
6
Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis.
Chemistry. 2016 Dec 19;22(51):18290-18315. doi: 10.1002/chem.201603382. Epub 2016 Sep 13.
7
Metal-Free Hydrosilylation of Ketenes with Silicon Electrophiles: Access to Fully Substituted Aldehyde-Derived Silyl Enol Ethers.
Chemistry. 2021 Jun 4;27(32):8273-8276. doi: 10.1002/chem.202100877. Epub 2021 May 6.
8
Mechanism of Mukaiyama-Michael Reaction of Ketene Silyl Acetal: Electron Transfer or Nucleophilic Addition?
J Org Chem. 1996 May 3;61(9):2951-2962. doi: 10.1021/jo9512968.
9
Synthesis of N-Heterocycle Substituted Silyl Ligands within the Coordination Sphere of Iron.
Organometallics. 2018 Sep 24;37(18):3024-3034. doi: 10.1021/acs.organomet.8b00399. Epub 2018 Sep 10.
10
Oxonia-cope prins cyclizations: a facile method for the synthesis of tetrahydropyranones bearing quaternary centers.
J Am Chem Soc. 2004 Dec 8;126(48):15662-3. doi: 10.1021/ja044736y.
引用本文的文献
1
An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.
Chem Sci. 2018 Feb 19;9(12):3221-3226. doi: 10.1039/c8sc00020d. eCollection 2018 Mar 28.
本文引用的文献
1
Stereoselective synthesis of the rocaglamide skeleton via a silyl vinylketene formation/[4 + 1] annulation sequence.
Org Lett. 2008 Oct 2;10(19):4215-8. doi: 10.1021/ol801435j. Epub 2008 Aug 28.
2
Synthesis of polysubstituted cyclopentenones via [4+1] reactions of TIPS-vinylketenes.
J Org Chem. 2007 Dec 21;72(26):10254-7. doi: 10.1021/jo702109e. Epub 2007 Nov 16.
3
Reactions of (trialkylsilyl)vinylketenes with lithium ynolates: a new benzannulation strategy.
Org Lett. 2005 Sep 1;7(18):3905-8. doi: 10.1021/ol051307b.
4
Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with alpha-benzotriazolyl organolithium compounds.
Angew Chem Int Ed Engl. 2005 Sep 12;44(36):5867-70. doi: 10.1002/anie.200501579.
5
Synthesis and reactivity of silyl vinylketenes: a formal interrupted Dötz benzannulation with unexpected silyl migration.
Org Lett. 2001 Oct 18;3(21):3389-91. doi: 10.1021/ol016615y.
6
Hetero [4 + 2] cycloadditions of (trialkylsilyl)vinylketenes. Synthesis of alpha,beta-unsaturated delta-valerolactones and -lactams.
Org Lett. 1999 Aug 26;1(4):641-4. doi: 10.1021/ol9907217.
Zotero 插件