富马酸烯丙酯的共轭加成/爱尔兰-克莱森重排反应：简便合成末端分化的琥珀酸酯类化合物
Conjugate addition/Ireland-Claisen rearrangements of allyl fumarates: simple access to terminally differentiated succinates.
作者信息
Bausch Cory C, Johnson Jeffrey S
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
J Org Chem. 2008 Feb 15;73(4):1575-7. doi: 10.1021/jo701778k. Epub 2008 Jan 23.
Abstract
The conjugate addition of dialkylzinc reagents to allyl fumarates with subsequent Ireland-Claisen rearrangement has been accomplished yielding substituted unsymmetrical succinic acid derivatives. This one-pot reaction creates two new carbon-carbon bonds at contiguous stereogenic centers. The reaction proceeds for several alkylzinc reagents and substituted allyl fumarates. The products contain distinguishable functional handles for further manipulation.
摘要
二烷基锌试剂与富马酸烯丙酯进行共轭加成，随后进行爱尔兰-克莱森重排，得到了取代的不对称琥珀酸衍生物。这种一锅法反应在相邻的手性中心形成了两个新的碳-碳键。该反应适用于多种烷基锌试剂和取代的富马酸烯丙酯。产物含有可区分的官能团，便于进一步操作。
相似文献
1
Conjugate addition/Ireland-Claisen rearrangements of allyl fumarates: simple access to terminally differentiated succinates.
J Org Chem. 2008 Feb 15;73(4):1575-7. doi: 10.1021/jo701778k. Epub 2008 Jan 23.
2
Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid.
J Org Chem. 2002 Mar 22;67(6):1738-45. doi: 10.1021/jo015501x.
3
Reactivity of dimethyl fumarate and methylhydrogen fumarate towards glutathione and N-acetyl-L-cysteine--preparation of S-substituted thiosuccinic acid esters.
Bioorg Med Chem. 2007 Jan 1;15(1):333-42. doi: 10.1016/j.bmc.2006.09.053. Epub 2006 Sep 29.
4
Gold(I) Catalyzed Dearomative Claisen Rearrangement of Allyl, Allenyl Methyl, and Propargyl Aryl Ethers.
Org Lett. 2017 Nov 17;19(22):6256-6259. doi: 10.1021/acs.orglett.7b03306. Epub 2017 Nov 7.
5
Preparation of chiral 3-arylpyrrolidines via the enantioselective 1,4-addition of arylboronic acids to fumaric esters catalyzed by Rh(I)/chiral diene complexes.
Org Lett. 2012 Jun 1;14(11):2766-9. doi: 10.1021/ol300980k. Epub 2012 May 17.
6
Unlocking the pH-responsive degradability of fumaramic acid derivatives using photoisomerization.
Chemistry. 2014 Nov 24;20(48):15715-8. doi: 10.1002/chem.201405205. Epub 2014 Oct 21.
7
Catalytic mechanisms of complex II enzymes: a structural perspective.
Biochim Biophys Acta. 2013 May;1827(5):648-57. doi: 10.1016/j.bbabio.2012.09.008. Epub 2012 Sep 18.
8
Revisiting Aromatic Claisen Rearrangement Using Unstable Aryl Sulfonium/Iodonium Species: The Strategy of Breaking Up the Whole into Parts.
Acc Chem Res. 2022 Aug 2;55(15):2103-2122. doi: 10.1021/acs.accounts.2c00263. Epub 2022 Jul 21.
9
Synthesis of α-(Pentafluorosulfanyl)- and α-(Trifluoromethyl)-Substituted Carboxylic Acid Derivatives by Ireland-Claisen Rearrangement.
J Org Chem. 2017 Feb 3;82(3):1638-1648. doi: 10.1021/acs.joc.6b02805. Epub 2017 Jan 12.
10
Mechanism of benzylsuccinate synthase: stereochemistry of toluene addition to fumarate and maleate.
J Am Chem Soc. 2005 Jun 22;127(24):8608-9. doi: 10.1021/ja051972f.
引用本文的文献
1
Photoredox-enabled 1,2-dialkylation of α-substituted acrylates Ireland-Claisen rearrangement.
Chem Sci. 2021 Jan 7;12(8):2816-2822. doi: 10.1039/d0sc06385a.
2
Copper-Catalyzed Dimerization/Cyclization of Itaconates.
Molecules. 2015 Aug 17;20(8):15023-32. doi: 10.3390/molecules200815023.
本文引用的文献
1
Catalytic asymmetric tandem transformations triggered by conjugate additions.
Angew Chem Int Ed Engl. 2006 Jan 9;45(3):354-66. doi: 10.1002/anie.200500195.
2
Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds.
Org Lett. 2004 Sep 16;6(19):3425-7. doi: 10.1021/ol048421z.
3
Development of a new Lewis acid-catalyzed [3,3]-sigmatropic rearrangement: the allenoate-Claisen rearrangement.
J Am Chem Soc. 2002 Nov 20;124(46):13646-7. doi: 10.1021/ja028090q.
4
Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.
Acc Chem Res. 2000 Jun;33(6):346-53. doi: 10.1021/ar990084k.
5
Diphenylphosphoryl azide. A new convenient reagent for a modified Curtus reaction and for the peptide synthesis.
J Am Chem Soc. 1972 Aug 23;94(17):6203-5. doi: 10.1021/ja00772a052.
Zotero 插件