手性环丙叉基酮：反应性和选择性的 Diels-Alder 二烯亲合物。
Chiral cyclopropenyl ketones: reactive and selective Diels-Alder dienophiles.
机构信息
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
出版信息
J Org Chem. 2013 Apr 5;78(7):3342-8. doi: 10.1021/jo302683t. Epub 2013 Mar 11.
Abstract
The synthesis and Diels-Alder reactions of cyclopropenyl ketones are described. Cyclopropenyl ketones are highly reactive dienophiles that can engage a range of cyclic dienes and 2,3-dimethylbutadiene. The strategy of using cyclopropenyl ketones to facilitate Diels-Alder reactions is not limited to products that contain three-membered rings, as reductive opening by SmI2 can be used to produce a product that lacks a cyclopropane but retains a quaternary stereogenic center.
摘要
描述了环丙烯酮的合成和 Diels-Alder 反应。环丙烯酮是一种高反应性的双烯体，可以与一系列环状二烯和 2,3-二甲基丁二烯发生反应。使用环丙烯酮促进 Diels-Alder 反应的策略不仅限于含有三元环的产物，因为 SmI2 的还原开环可以用于生成缺少环丙烷但保留季立体中心的产物。
相似文献
1
Chiral cyclopropenyl ketones: reactive and selective Diels-Alder dienophiles.手性环丙叉基酮：反应性和选择性的 Diels-Alder 二烯亲合物。
J Org Chem. 2013 Apr 5;78(7):3342-8. doi: 10.1021/jo302683t. Epub 2013 Mar 11.
2
Oxazaborolidinone-catalyzed enantioselective Diels-Alder reaction of acyclic alpha,beta-unsaturated ketones.恶唑硼烷酮催化的无环α,β-不饱和酮的对映选择性狄尔斯-阿尔德反应
J Org Chem. 2008 Jan 4;73(1):212-8. doi: 10.1021/jo702043g. Epub 2007 Dec 6.
3
Fast, irreversible modification of cysteines through strain releasing conjugate additions of cyclopropenyl ketones.通过释放应变的环丙烯酮共轭加成，快速不可逆地修饰半胱氨酸。
Org Biomol Chem. 2018 Mar 28;16(12):2164-2169. doi: 10.1039/c8ob00166a. Epub 2018 Mar 9.
4
Aminocatalytic asymmetric Diels-Alder reactions via HOMO activation.通过 HOMO 活化的手性氨基催化不对称 Diels-Alder 反应。
Acc Chem Res. 2012 Sep 18;45(9):1491-500. doi: 10.1021/ar3000822. Epub 2012 Jun 20.
5
Diels-Alder exo selectivity in terminal-substituted dienes and dienophiles: experimental discoveries and computational explanations.末端取代二烯和亲双烯体中狄尔斯-阿尔德反应的外型选择性：实验发现与计算解释
J Am Chem Soc. 2009 Feb 11;131(5):1947-57. doi: 10.1021/ja8079548.
6
Reaction of Aldehydes/Ketones with Electron-Deficient 1,3,5-Triazines Leading to Functionalized Pyrimidines as Diels-Alder/Retro-Diels-Alder Reaction Products: Reaction Development and Mechanistic Studies.醛/酮与缺电子 1,3,5-三嗪反应生成功能化嘧啶作为 Diels-Alder/Retro-Diels-Alder 反应产物：反应开发和机理研究。
J Org Chem. 2017 Mar 3;82(5):2336-2344. doi: 10.1021/acs.joc.6b02570. Epub 2017 Feb 10.
7
Bioinspired intramolecular Diels-Alder reaction: a rapid access to the highly-strained cyclopropane-fused polycyclic skeleton.生物启发的分子内狄尔斯-阿尔德反应：快速构建高度张力的环丙烷稠合多环骨架。
Chemistry. 2014 Feb 24;20(9):2425-30. doi: 10.1002/chem.201304839. Epub 2014 Feb 5.
8
Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels-Alder reaction of β,γ-unsaturated α-keto esters.通过β，γ-不饱和α-酮酯的二烯传递杂环狄尔斯-阿尔德反应立体控制合成多杂环化合物。
Org Biomol Chem. 2015 Jun 7;13(21):5875-9. doi: 10.1039/c5ob00503e.
9
Study of very reactive tautomeric phenol dienones as dienes in Diels-Alder reactions.在狄尔斯-阿尔德反应中作为双烯体的高活性互变异构酚二烯酮的研究。
Org Lett. 2009 Mar 19;11(6):1197-200. doi: 10.1021/ol8026768.
10
Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones.1,3-烯炔与酮的高度区域选择性催化不对称还原偶联反应。
Org Lett. 2005 Jul 7;7(14):3077-80. doi: 10.1021/ol051075g.
引用本文的文献
1
Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.通过环丙烯与氨基环丙烷的(3 + 2)环化反应合成双环[3.1.0]己烷。
Chem Sci. 2019 Oct 8;10(46):10716-10722. doi: 10.1039/c9sc03790j. eCollection 2019 Dec 14.
2
A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate.一种光笼蔽的、含环丙烯的氨基酸神经递质谷氨酸类似物。
Tetrahedron Lett. 2016 Dec 21;57(51):5750-5752. doi: 10.1016/j.tetlet.2016.10.106. Epub 2016 Nov 11.
3
Fast, irreversible modification of cysteines through strain releasing conjugate additions of cyclopropenyl ketones.通过释放应变的环丙烯酮共轭加成，快速不可逆地修饰半胱氨酸。
Org Biomol Chem. 2018 Mar 28;16(12):2164-2169. doi: 10.1039/c8ob00166a. Epub 2018 Mar 9.
本文引用的文献
1
Gold(I)-catalyzed asymmetric cyclopropenation of internal alkynes.金（I）催化的内炔不对称环丙烷化反应。
J Am Chem Soc. 2012 Jul 25;134(29):11916-9. doi: 10.1021/ja304506g. Epub 2012 Jul 9.
2
Highly enantioselective cyclopropenation reaction of 1-alkynes with α-alkyl-α-diazoesters catalyzed by dirhodium(II) carboxylates.由羧酸铑（II）催化的1-炔烃与α-烷基-α-重氮酯的高度对映选择性环丙烷化反应。
Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6803-8. doi: 10.1002/anie.201101905. Epub 2011 Jun 14.
3
Enantioselective cyclopropenation of alkynes with acceptor/acceptor-substituted diazo reagents via Co(II)-based metalloradical catalysis.通过基于钴(II)的金属自由基催化，手性环丙炔化试剂与受体/受体取代的重氮试剂的炔烃的对映选择性环丙烷化。
J Am Chem Soc. 2011 Mar 16;133(10):3304-7. doi: 10.1021/ja111334j. Epub 2011 Feb 18.
4
Enantioenriched synthesis of cyclopropenes with a quaternary stereocenter, versatile building blocks.对映富集合成具有季立体中心的环丙烯，多功能构建块。
J Am Chem Soc. 2011 Jan 19;133(2):170-1. doi: 10.1021/ja1089217. Epub 2010 Oct 29.
5
Intramolecular Diels-Alder reactions of cyclopropenone ketals.环丙叉酮缩醛的分子内 Diels-Alder 反应。
Org Lett. 2010 Aug 6;12(15):3540-3. doi: 10.1021/ol101375a.
6
Rhodium-catalyzed cyclopropenation of alkynes: synthesis of trifluoromethyl-substituted cyclopropenes.铑催化的炔烃环丙烷化反应：三氟甲基取代环丙烯的合成
Angew Chem Int Ed Engl. 2010 Jun 7;49(25):4294-6. doi: 10.1002/anie.201000787.
7
The Diels--Alder reaction in total synthesis.狄尔斯-阿尔德反应在全合成中的应用
Angew Chem Int Ed Engl. 2002 May 17;41(10):1668-98. doi: 10.1002/1521-3773(20020517)41:10<1668::aid-anie1668>3.0.co;2-z.
8
Intramolecular cyclopropene-furan [2 + 4] cycloaddition followed by a cyclopropylcarbinyl rearrangement to synthesize the BCD rings of cortistatin A.分子内环丙烯 - 呋喃[2 + 4]环加成反应，随后进行环丙基甲基重排以合成可替他汀A的BCD环。
Org Lett. 2009 Sep 3;11(17):3938-41. doi: 10.1021/ol901537n.
9
Efficient synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones via the PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols.通过PdCl₂催化的2,3-或3,4-联烯醇的氯环羰基化反应高效合成3-氯甲基-2(5H)-呋喃酮和3-氯甲基-5,6-二氢吡喃-2-酮。
J Org Chem. 2008 Nov 21;73(22):8960-5. doi: 10.1021/jo8015677. Epub 2008 Oct 22.
10
Studies on the stability of cycloprop-2-ene carboxylate dianions and reactions with electrophiles.环丙烷 -2- 烯羧酸盐二价阴离子的稳定性及与亲电试剂反应的研究。
J Org Chem. 2008 Nov 7;73(21):8474-8. doi: 10.1021/jo801683n. Epub 2008 Oct 14.
Zotero 插件