通过顺序的 Brook 和 Ireland-Claisen 重排合成γ，δ-不饱和乙醇酸。
Synthesis of gamma,delta-unsaturated glycolic acids via sequenced brook and Ireland--claisen rearrangements.
机构信息
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
出版信息
Org Lett. 2010 Mar 5;12(5):944-7. doi: 10.1021/ol9029353.
Abstract
Organozinc, -magnesium, and -lithium nucleophiles initiate a Brook/Ireland-Claisen rearrangement sequence of allylic silyl glyoxylates resulting in the formation of gamma,delta-unsaturated alpha-silyloxy acids.
摘要
有机锌、-镁和-lithium 亲核试剂引发烯丙基硅基乙二醛酸酯的 Brook/Ireland-Claisen 重排序列，生成 γ,δ-不饱和 α-硅氧基酸。
相似文献
1
Synthesis of gamma,delta-unsaturated glycolic acids via sequenced brook and Ireland--claisen rearrangements.通过顺序的 Brook 和 Ireland-Claisen 重排合成γ，δ-不饱和乙醇酸。
Org Lett. 2010 Mar 5;12(5):944-7. doi: 10.1021/ol9029353.
2
Synthesis of Alkylidene(gem-Difluorocyclopropanes) from Propargyl Glycolates by a One-Pot Difluorocyclopropenation/Ireland-Claisen Rearrangement Sequence.通过一锅法二氟环丙烯化/Ireland-Claisen 重排序列，由炔丙基丙二酸盐合成亚烷基（偕二氟环丙基）。
J Org Chem. 2017 Apr 7;82(7):3965-3975. doi: 10.1021/acs.joc.7b00197. Epub 2017 Mar 24.
3
Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.通过硅基乙二醛的 Reformatsky/Claisen 缩合反应，对裂环烯醚萜内酯 B 进行了正规合成。
Org Lett. 2011 Jun 17;13(12):3206-9. doi: 10.1021/ol2011192. Epub 2011 May 17.
4
Self-consistent synthesis of the squalene synthase inhibitor zaragozic acid C via controlled oligomerization.通过可控低聚反应自洽合成角鲨烯合酶抑制剂zaragozic acid C。
J Am Chem Soc. 2008 Dec 24;130(51):17281-3. doi: 10.1021/ja808347q.
5
Organobase-catalyzed [1,2]-Brook rearrangement of silyl glyoxylates.有机碱催化的甲硅烷基乙醛酸酯的[1,2]-布鲁克重排反应。
Org Biomol Chem. 2017 Feb 7;15(6):1418-1425. doi: 10.1039/c7ob00005g.
6
Copper-Catalyzed Reductive Ireland-Claisen Rearrangements of Propargylic Acrylates and Allylic Allenoates.铜催化的丙炔酸酯和烯丙基丙二烯酸酯的还原 Ireland-Claisen 重排反应。
J Org Chem. 2022 Jan 7;87(1):429-452. doi: 10.1021/acs.joc.1c02455. Epub 2021 Dec 17.
7
Highly Stereoselective Synthesis of Trifluoromethylated Compounds via Ester-Enolate [2,3]-Wittig and [3,3]-Ireland-Claisen Rearrangements.通过酯烯醇盐[2,3]-维蒂希重排和[3,3]-爱尔兰-克莱森重排实现三氟甲基化化合物的高度立体选择性合成。
J Org Chem. 1997 Jan 10;62(1):137-150. doi: 10.1021/jo961246i.
8
Claisen rearrangements of equilibrating allylic azides.平衡烯丙基叠氮化物的克莱森重排。
Org Biomol Chem. 2011 Oct 21;9(20):7057-61. doi: 10.1039/c1ob05972f. Epub 2011 Aug 30.
9
Catalytic redox-initiated glycolate aldol additions of silyl glyoxylates.催化氧化还原引发的甲硅烷基乙醛酸酯的乙醇酸酯醛醇加成反应。
Org Lett. 2009 Feb 19;11(4):827-30. doi: 10.1021/ol802828d.
10
Quantitative structure-activity relationships involving the inhibition of glycolic acid oxidase by derivatives of glycolic and glyoxylic acids.涉及乙醇酸和乙醛酸衍生物对乙醇酸氧化酶抑制作用的定量构效关系。
J Med Chem. 1979 Jun;22(6):608-14. doi: 10.1021/jm00192a002.
引用本文的文献
1
Rhodium-Catalyzed Asymmetric Arylation-Induced Glycolate Aldol Additions of Silyl Glyoxylates.铑催化的甲硅烷基乙醛酸酯的不对称芳基化诱导乙醇酸酯醛醇加成反应
Angew Chem Int Ed Engl. 2023 Oct 16;62(42):e202311554. doi: 10.1002/anie.202311554. Epub 2023 Sep 12.
2
Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.二硼甲烷的立体选择性串联双亲电偶联反应。
J Am Chem Soc. 2017 Oct 11;139(40):14061-14064. doi: 10.1021/jacs.7b09309. Epub 2017 Sep 27.
3
An Asymmetric Vinylogous Michael Cascade of Silyl Glyoximide, Vinyl Grignard, and Nitroalkenes via Long Range Stereoinduction.通过远程立体诱导实现的甲硅烷基乙二酰亚胺、乙烯基格氏试剂和硝基烯烃的不对称乙烯型迈克尔串联反应。
J Org Chem. 2016 Feb 19;81(4):1712-7. doi: 10.1021/acs.joc.5b02693. Epub 2016 Feb 2.
4
Alternaric acid: formal synthesis and related studies.交替酸的全合成及相关研究。
Beilstein J Org Chem. 2013;9:166-72. doi: 10.3762/bjoc.9.19. Epub 2013 Jan 24.
5
Base-catalyzed direct aldolization of α-alkyl-α-hydroxy trialkyl phosphonoacetates.α-烷基-α-羟基三烷基膦酸酯的碱催化直接羟醛缩合反应。
Angew Chem Int Ed Engl. 2012 May 7;51(19):4685-9. doi: 10.1002/anie.201200559. Epub 2012 Apr 4.
6
Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.硅基乙二醛酸酯。多组分偶联用柔性连接试剂的构思与实现。
J Org Chem. 2012 May 18;77(10):4503-15. doi: 10.1021/jo300184h. Epub 2012 Mar 23.
7
Three-component glycolate Michael reactions of enolates, silyl glyoxylates, and α,β-enones.烯醇盐、硅基乙二醛和α,β-烯酮的三组分乙二醇迈克尔加成反应。
J Org Chem. 2012 Apr 6;77(7):3246-51. doi: 10.1021/jo202679u. Epub 2012 Mar 15.
8
Construction of cyclopentanol derivatives via three-component coupling of silyl glyoxylates, acetylides, and nitroalkenes.通过硅基乙二醛酯、炔烃和硝基烯烃的三组分偶联反应构建环戊醇衍生物。
Org Lett. 2012 Jan 20;14(2):652-5. doi: 10.1021/ol2033527. Epub 2012 Jan 11.
9
Three-component coupling approach to trachyspic acid.三步耦联法合成 Trachyspic acid。
Org Lett. 2011 Oct 7;13(19):5136-9. doi: 10.1021/ol202002r. Epub 2011 Aug 31.
10
Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.远程立体诱导全取代烯醇盐的酰化反应：硅基乙二醛酸酯和β-内酰胺的串联 Reformatsky/季碳 Claisen 缩合反应。
J Am Chem Soc. 2010 Dec 15;132(49):17393-5. doi: 10.1021/ja108848d. Epub 2010 Nov 18.
本文引用的文献
1
Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.硅烯转移至α-酮酯及其在γ-内酯合成中的应用。
Tetrahedron. 2009 Sep 1;65(33):6447-6453. doi: 10.1016/j.tet.2009.05.066.
2
Diastereodivergent addition of allenylzincs to aryl glyoxylates.烯丙基锌对芳基乙醛酸酯的非对映发散性加成反应。
Org Lett. 2009 Jun 4;11(11):2397-400. doi: 10.1021/ol900494g.
3
Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.通过双Reformatsky反应从甲硅烷基乙醛酸酯和酮非对映选择性合成五取代γ-丁内酯。
Angew Chem Int Ed Engl. 2009;48(20):3689-91. doi: 10.1002/anie.200900215.
4
Synthesis of tertiary alpha-hydroxy acids by silylene transfer to alpha-keto esters.通过硅烯转移至α-酮酯合成叔α-羟基酸。
Org Lett. 2007 Oct 25;9(22):4651-3. doi: 10.1021/ol702148x. Epub 2007 Oct 2.
5
Three-component coupling reactions of silylglyoxylates, alkynes, and aldehydes: a chemoselective one-step glycolate aldol construction.甲硅烷基乙醛酸酯、炔烃和醛的三组分偶联反应：化学选择性一步构建乙醇酸酯缩醛醇
J Am Chem Soc. 2005 May 4;127(17):6170-1. doi: 10.1021/ja043884l.
6
Silylene transfer to carbonyl compounds and subsequent Ireland-Claisen rearrangements to control formation of quaternary carbon stereocenters.硅烯转移至羰基化合物并随后进行爱尔兰-克莱森重排以控制季碳立体中心的形成。
J Am Chem Soc. 2005 Feb 23;127(7):2046-7. doi: 10.1021/ja042893r.
7
Catalytic diastereoselective reductive claisen rearrangement.
Org Lett. 2002 Aug 8;4(16):2743-5. doi: 10.1021/ol026273b.
8
The Cu(OTf)2- and Yb(OTf)3-catalyzed Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers.Cu(OTf)₂和Yb(OTf)₃催化的2-烷氧羰基取代的烯丙基乙烯基醚的克莱森重排反应
Org Lett. 2001 Jan 11;3(1):49-52. doi: 10.1021/ol006760w.
Zotero 插件