Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides

论文摘要

A highly diastereoselective and enantioselective Michael addition/desymmetrization reaction of maleimides with prochiral 3-substituted phthalides catalyzed by quinine-derived bifunctional thiourea was realized. A broad range of the 3,3′-disubstituted phthalides bearing vicinal quaternary-tertiary stereogenic centers were synthesized in moderate to good yields（up to 96%） with high diastereoselectivities（up to >19:1 dr） and enantioselectivities（up to 96:4 er）.

论文目录

文章来源

类型: 期刊论文

作者: Jie Wang,Xin Li,Jin-Pei Cheng

来源: Science China(Chemistry) 2019年05期

年度: 2019

分类: 工程科技Ⅰ辑

专业: 化学

单位: State Key Laboratory of Elemento-Organic Chemistry,Collaborative Innovation Center of Chemical Science and Engineering,College of Chemistry,Nankai University

基金: supported by the National Natural Science Foundation of China(21390400)

分类号: O621.25

页码: 649-652

总页数: 4

文件大小: 364K

下载量: 10

相关论文文献

• [1].Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction[J]. Chinese Chemical Letters 2017(08)
• [2].Structural and Spectroscopic Study on Complexation of Cm(Ⅲ) with TMOGA in Aqueous Solution[J]. Annual Report of China Institute of Atomic Energy 2016(00)
• [3].Structural,electronic,and magnetic behaviors of 5d transition metal atom substituted divacancy graphene:A first-principles study[J]. Chinese Physics B 2017(05)
• [4].One-pot and novel route for the synthesis of 4-substituted-1,2,4-triazolidine-3,5-diones[J]. Chinese Chemical Letters 2014(03)
• [5].Asymmetric synthesis of pyrrolo[1,2-a]indoles via organocatalytic[3+2]annulation of substituted 2-vinylindoles with azlactones[J]. Chinese Chemical Letters 2020(03)
• [6].Investigation of L/D-threonine substituted L-serine octamer ions by mass spectrometry and infrared photodissociation spectroscopy[J]. Chinese Chemical Letters 2017(03)
• [7].Tetra-EDOT substituted 3D electrochromic polymers with lower band gaps[J]. Science China(Chemistry) 2017(01)
• [8].Improved thermoelectric property of cation-substituted CaMnO_3[J]. Chinese Physics B 2015(09)
• [9].Cyclization and halogenation of substituted o-allylphenols with diacetoxyiodobenzene in the presence of iodine or bromine[J]. Chinese Chemical Letters 2008(06)
• [10].Synthesis and anti-inflammatory activity of 2-substituted-((N,N-disubstituted)-1,3-benzoxazole)-5-carboxamides[J]. 药学学报 2010(06)
• [11].A new method for the synthesis of N-substituted pyrroles[J]. Chinese Chemical Letters 2010(11)
• [12].Glycerol mediated synthesis of 5-substituted lH-tetrazole under catalyst free conditions[J]. Chinese Chemical Letters 2012(02)
• [13].Charge Transport Properties of Tetrabenz[a,c,h,j]-anthracene Derivatives[J]. 结构化学 2012(06)
• [14].Synthesis and biological evaluation of some novel-3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines[J]. Chinese Chemical Letters 2010(10)
• [15].Ammonium metavanadate:A novel catalyst for synthesis of 2-substituted benzimidazole derivatives[J]. Chinese Chemical Letters 2009(03)
• [16].Magnetic properties of La-Zn substituted Sr-hexaferrites by self-propagation high-temperature synthesis[J]. Journal of Rare Earths 2008(01)
• [17].Facile synthesis of CF_3-substituted dienamides via one-pot tandem reactions[J]. Chinese Chemical Letters 2017(07)
• [18].Synthesis and cytotoxic activity of 3-phenyl-4-substituted-β-carbolines[J]. Chinese Chemical Letters 2012(11)
• [19].Synthesis and anti-HBV activity of novel 5-substituted pyridin-2(1H)-one derivatives[J]. Chinese Chemical Letters 2010(03)
• [20].Facile and efficient synthesis of 2-substituted-Nl-carbethoxy-2,3-dihydro-4(1H)-quinazolinones in fluorous solvent[J]. Chinese Chemical Letters 2008(05)
• [21].Preparation, Structure and Electrochemical Property of a Pyrazole-substituted Diiron Dithiolate Complex[J]. 结构化学 2012(11)
• [22].Silica chloride catalyzed one-pot synthesis of fully substituted pyrazoles[J]. Chinese Chemical Letters 2011(10)
• [23].Synthesis of 2-Phenyl-10-substituted Hymenialdisine Derivatives[J]. Chemical Research in Chinese Universities 2011(06)
• [24].Synthesis and electronic properties of expanded 5-(hetero)arylthien-2-yl substituted 3-ethynyl quinoxalines with AIE characteristics[J]. Science China(Chemistry) 2018(08)
• [25].Synthesis of N-substituted-2-aminobenzothiazoles using nano copper oxide as a recyclable catalyst under ligand-free conditions in reusable PEG-400 medium[J]. Chinese Chemical Letters 2014(05)
• [26].Thermoelectric properties of Al substituted misfit cobaltite Ca_3(Co_(1-x)Al_x)_4O_9 at low temperature[J]. International Journal of Minerals Metallurgy and Materials 2014(07)
• [27].Asymmetric aza-Henry reaction with α-substituted nitroacetates catalyzed by a bifunctional thiourea-guanidine catalyst[J]. Chinese Chemical Letters 2011(08)
• [28].A convenient synthesis of methyl 2-hydroxy-4-oxo-4-(substituted phenyl) butanoates from malic acid[J]. Chinese Chemical Letters 2009(08)
• [29].Study on the quantitative structureactivity relation-ship of C-10 substituted artemisinin (QHS)’s derivatives using rough set theory[J]. Science in China(Series B:Chemistry) 2008(10)
• [30].Stereochemical determination of tetrahydropyran-substituted xanthones from fungus Chaetomium murorum[J]. Chinese Chemical Letters 2015(12)