固载化L-脯氨酸及其衍生物的最新研究进展
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摘要
近年来,固载化L-脯氨酸及其衍生物手性催化剂因其具有均相催化剂的高活性和高选择性以及非均相催化剂的高循环使用性,被广泛用于催化不对称有机化学反应。本文简单介绍了L-脯氨酸及其衍生物的种类,包括4-羟基-L-脯氨酸、脯氨醇醚类等;重点阐述了固载L-脯氨酸类催化剂的载体类型和固载方法,催化剂载体类型主要包括离子液体、无机纳米粒子、有机聚合物以及新出现的聚合物离子液体和有机-无机杂化微球,固载方法主要包括硅烷化反应法、点击化学法以及可逆加成-断裂链转移(RAFT)聚合法,并对不同载体及固载方法的优缺点进行了总结。最后,针对目前固载化L-脯氨酸类催化剂存在的问题进行了原因分析并提出了改进建议,为以后新型固载化催化剂的研究开发提供了可能。
In recent years, supported L-proline and its derivatives are widely used as promising chiral catalysts in asymmetric organic chemical reactions owing to their high selectivity and reusability. This paper briefly introduces the types of L-proline and its derivatives. This paper also illustrates the types of the catalyst support, including ionic liquid, inorganic nanoparticles, organic polymer, ionic liquid-polymer and organic-inorganic hybrid microspheres. Additionally, this paper describes differentimmobilization methods of L-proline, including click chemistry and RAFT polymerization, together withtheir advantages and disadvantages and the improvement recommendations. The suggestions and prospects provide useful information for the preparation of novel immobilized catalysts, which have high activity, selectivity and excellent reusability in asymmetric reaction.
In recent years, supported L-proline and its derivatives are widely used as promising chiral catalysts in asymmetric organic chemical reactions owing to their high selectivity and reusability. This paper briefly introduces the types of L-proline and its derivatives. This paper also illustrates the types of the catalyst support, including ionic liquid, inorganic nanoparticles, organic polymer, ionic liquid-polymer and organic-inorganic hybrid microspheres. Additionally, this paper describes differentimmobilization methods of L-proline, including click chemistry and RAFT polymerization, together withtheir advantages and disadvantages and the improvement recommendations. The suggestions and prospects provide useful information for the preparation of novel immobilized catalysts, which have high activity, selectivity and excellent reusability in asymmetric reaction.
引文
[1] LIST B, LERNER R A, BARBAS C F. Proline-catalyzed directasymmetric aldol reactions[J]. Journal of the American ChemicalSociety, 2000, 122:2395-2396.
[2] ELMEKAWY A A, SWEENEY J B, BROWN D R. Efficient synthesisof supported proline catalysts for asymmetric aldol reactions[J].Catalysis Science&Technology, 2015, 5:690-696.
[3] HALSKOV K S, DONSLUND B S, PAZ B M, et al. Computationalapproach to diarylprolinol-silyl ethers in aminocatalysis[J]. Accountsof Chemical Research, 2016, 49(5):974-986.
[4] KUMAR T P, BALAJI S V. Sugar amide-pyrrolidine catalyst for theasymmetric Michael addition of ketones to nitroolefins[J]. Tetrahedron:Asymmetry, 2014, 25:473-477.
[5] JORRES M, MERSMANN S, RAABE G, et al. Organocatalyticsolvent-free hydrogen bondingmediated asymmetric Michael additionsunder ball milling conditions[J]. Green Chemistry, 2013, 15:612-616.
[6] CHO E, LEE H, KIM T H. Asymmetric aldol aeaction aatalyzed by L-proline and achiral thiourea fluoroboric acid salt[J]. Bulletin of theKorean Chemical Society, 2015, 36:410-412.
[7] ELMANSY M F, KANG J Y, LINGAMPALLY R, et al. Prolinesulfonamide-catalyzed, domino process for asymmetric synthesis ofamino and hydroxy-substituted bicyclo[2.2.2]octanes[J]. EuropeanJournal of Organic Chemistry, 2016(1):150-157.
[8] LI X J, YANG B L, ZHANG S L, et al. Facile synthesis of hairymicroparticle-/nanoparticle-supported MacMillan and its applicationto Diels-Alder reaction in water[J]. Colloid and Polymer Science,2017, 295:573-582.
[9] RUEPING M, KUENKEL A, TATO F, et al. Asymmetricorganocatalytic domino Michael/Aldol reactions:enantioselectivesynthesis of chiral cycloheptanones, tetrahydrochromenones, andpolyfunctionalized bicyclo-[3.2.1]octanes[J]. Angewandte Chemie-International Edition, 2009, 48:3699-3702.
[10] AN Q J, SHEN J F, BUTT N, et al. Asymmetric domino doubleMichael addition of nitroolefins and aldehyde esters with trans-perhydroindolic acid as an organocatalyst[J]. Synthesis-Stuttgart,2013, 45:1612-1623.
[11] LI X J, ZHANG S L, YANG B L, et al. Magnetic Fe3O4nanoparticlessupporting Macmillan with controlled shell structure as an efficientand reusable catalyst for asymmetric reaction[J]. RSC Advances, 2016,6:86531-86539.
[12] LI J, LI X B, MA S S, et al. An ionic liquid containing L-prolinemoiety as highly efficient and recyclable chiral organocatalyst forMichael addition[J]. Bulletin of the Korean Chemical Society, 2016,37:1259-1264.
[13] ZHANG J L, ZHANG M X, TANG K J, et al. Polymer-based stimuli-responsive recyclable catalytic systems for organic synthesis[J]. Small,2014, 10(1):32-46.
[14] XU Y, HUA Z, ZHANG J, et al. Mimicking enzymatic systems:modulation of the performance of polymeric organocatalysts by ion-specific effects[J]. Chemical Communications, 2016, 52:3392-3395.
[15] NI B K, ZHANG Q Y, DHUNGANA K, et al. Ionic liquid-supported(ILs)(S)-pyrrolidine sulfonamide, a recyclable organocatalyst for thehighly enantioselective Michael addition to nitroolefins[J]. OrganicLetters, 2009, 11(4):1037-1040.
[16] YADAV G D, SINGH S. prolinamide imidazoliumhexafluorophosphate ionic liquid as an efficient reusableorganocatalyst for direct asymmetric aldol reaction in solvent-freecondition[J]. RSC Advances, 2016, 6:100459-100466.
[17] LI X J, LV C N, JIA X B, et al. Nanoparticle based on poly(ionicliquid)as an efficient solid immobilization catalyst for Aldol reactionand multicomponent reaction in water[J]. ACS Applied Materials&Interfaces, 2017, 9:827-835.
[18]汪彩虹,陈硕然,叶常青,等.单分散磁性Fe3O4纳米粒子的研究进展[J].化工进展, 2016, 35(s1):242-247.WANG C H, CHEN S R, YE C Q, et al. Research progress onmonodisperse Fe3O4magnetic nanoparticles[J]. Chemical Industry andEngineering Progress, 2016, 35(s1):242-247.
[19] KHALAFI-NEZHAD A, NOURISEFAT M, PANAHI F. L-proline-modified magnetic nanoparticles(LPMNP):a novel magneticallyseparable organocatalyst[J]. RSC Advances, 2014, 4:22497-22500.
[20] SAFAEI-GHOMI J, AHEDI S. Diastereoselective synthesis ofisoxazolidines and spiroisoxazolidines via catalytic 1, 3-dipolarcycloaddition reactions in the presence of Fe3O4-L-prolinenanoparticles as a magnetic organocatalyst[J]. Tetrahedron Letters, 2016,57:1071-1073.
[21] KUMAR A, DEWAN M, DE A. Aldol condensation in PEG-400catalyzed by recyclable L-proline supported on nano gold surface[J].RSC Advances, 2013, 3:603-607.
[22] ZHAO Y B, ZHANG L W, WU L Y, et al. Silica-supportedpyrrolidine-triazole, an insoluble, recyclable organocatalyst for theenantioselective Michael addition of ketones to nitroalkenes[J].Tetrahedron:Asymmetry, 2008, 19:1352-1355.
[23] RIENTE P, MENDOZA C, PERICAS M A. Functionalization of Fe3O4magnetic nanoparticles for organocatalytic Michael reactions[J].Journal of Materials Chemistry, 2011, 21:7350-7355.
[24] SAFAEI-GHOMI J, ZAHEDI S. L-proline-functionalized Fe3O4nanoparticles as a novel magnetic chiral catalyst for the directasymmetric Mannich reaction[J]. Applied Organometallic Chemistry,2015, 29:566-571.
[25] KONG Y, TAN R, ZHAO L, et al. L-proline supported on ionic liquid-modified magnetic nanoparticles as a highly efficient and reusableorganocatalyst for direct asymmetric aldol reaction in water[J]. GreenChemistry, 2013, 15:2422-2433.
[26] ALZA E, AYALERO S, KASAPLAR P, et al. Polystyrene-supporteddiarylprolinol ethers as highly efficient organocatalysts for michael-type reactions[J]. Chemistry-A European Journal, 2011, 17:11585-11595.
[27] AKAGAWA K, SAKAMOTO S, KUDO K. Direct asymmetric aldolreaction in aqueous media using polymer-supported peptide[J].Tetrahedron Letters, 2005, 46:8185-8187.
[28] ZAYAS H A, LU A, VALADE D, et al. Thermoresponsive polymer-supported L-proline micelle catalysts for the direct asymmetric aldolreaction in water[J]. ACS Macro Letters, 2013, 2:327-331.
[29] HUERTA E, GENABEEK B V, STALS P J M, et al. A modularapproach to introduce function into single-chain polymeric nanoparticles[J]. Rapid Communications in Mass Spectrometry, 2014,35:1320-1325.
[30] LU A, MOATSOU D, HANDS-PORTMAN I, et al. Recyclable L-proline functional nanoreactors with temperature tuned activity basedon core-shell nanogels[J]. ACS Macro Letters, 2014, 3:1235-1239.
[31] LLANES P, SAYALERO S, RODRIGUEZ-ESCRICHA C, et al.Asymmetric cross-and self-aldol reactions of aldehydes in water witha polystyrene-supported triazolylproline organocatalyst[J]. GreenChemistry, 2016, 18:3507-3512.
[32] HE T, LI K, WU M Y, et al. Water promoted enantioselective Aldolreaction by proline cholesterol and-diosgenin based amphiphilicorganocatalysts[J]. Tetrahedron, 2013, 69:5136-5143.
[33] ARIVALAGAN P R, ZHAO Y. Interfacial catalysis of aldol reactionsby prolinamide surfactants in reverse micelles[J]. Organic&Biomolecular Chemistry, 2015, 13:770-775.
[34] LU A, COTANDA P, PATTERSON J P, et al. Aldol reactions catalyzedby L-proline functionalized polymeric nanoreactors in water[J].Chemical Communications, 2012, 48:9699-9701.
[35] LI X J, YANG B L, JIA X B, et al. Temperature-responsive hairyparticle-supported proline for direct asymmetric aldol reaction in water[J]. RSC Advances, 2015, 5:89149-89156.
[36] LU A, MOATSOU D, LONGBOTTOM D A, et al. Tuning the catalyticactivity of L-proline functionalized hydrophobic nanogel particles inwater[J]. Chemical Science, 2013, 4:965-969.
[37]焦彩彬,陈连喜,江杨,等. SiO2/聚合物复合粒子研究进展[J].材料导报A, 2015, 29(6):70-75.JIAO C B, CHEN L X, JIANG Y, et al. Progress of silica/polymercomposite nanoparticles[J]. Materials Review, 2015, 29(6):70-75.
[38] YANG H L, LI S W, WANG X Y, et al. Core-shell silica magneticmicrospheres supported proline as a recyclable organocatalyst for theasymmetric aldol reaction[j]. Journal of Molecular Catalysis A-Chemical, 2012, 364:404-410.
[39] WU T, FENG D D, XIE B, et al. A solution to achieve good reusabilityof MNPs Fe3O4-supported(S)-diphenylprolinoltrimethylsilyl ethercatalysts in asymmetric Michael reactions[J]. RSC Advances, 2016, 6:25246-25254.
[40]徐源鸿,熊兴泉,蔡雷,等.巯基-烯点击化学[J].化学进展, 2012, 24(s1):386-394.XU Y H, XIONG X Q, CAI Lei, et al. Thiol-ene click chemistry[J].Progress in Chemistry, 2012, 24(s1):386-394.
[41]蔡雷,熊兴泉,唐忠科,等.基于巯基-炔的“点击”化学研究进展[J].化工进展, 2011, 30(9):1982-1989.CAI L, XIONG X Q, TANG Z K, et al. Research progress of thiol-yneclick chemistry[J]. Chemical Industry and Engineering Progress, 2011,30(9):1982-1989.
[42] XIA A B, ZHANG C, ZHANG Y P, et al. J?rgensen-Hayashi catalystssupported on poly(ethylene glycol)s as highly efficient and reusableorganocatalysts for the enaminecatalyzed asymmetric Michael reaction[J]. Organic&Biomolecular Chemistry, 2015, 13:9593-9599.
[43] GURYEV A A, ANOKHIN M V, AVERIN A D, et al. Polymer-immobilized aa, aa-bis[bis-3, 5-(trifluoromethyl)phenyl]prolinol silylether:synthesis and application in the asymmetric aa-amination ofaldehydes[J]. Mendeleev Communications, 2015, 25:410-411.
[44] GURYEV A A, ANOKHIN M V, AVERIN A D, et al. HeterogeneousJ?rgensen-Hayashi catalyst for asymmetric Michael addition ofmalonates to a,b-enals. Cooperative effect with Ca(OTf)2[J]. MendeleevCommunications, 2016, 26:469-470.
[45] EVANS A C, LU A, ONDECK C, et al. Organocatalytic tunable aminoacid polymers prepared by controlled radical polymerization[J].Macromolecules, 2010, 43(15):6374-6380.
[46] BOYER C, BULMUS V, PRIYANTO P, et al. The stabilization andbio-functionalization of iron oxide nanoparticles using heterotelechelicpolymers[J]. Journal of Materials Chemistry, 2009, 19:111-123.
[47]吴鹏,申迎华,耿文博,等.多重响应性杂臂星型聚合物的RAFT聚合合成及性能研究[J].高分子学报, 2015(9):1114-1120.WU P, SHEN Y H, GENG W B, et al. Synthesis of multi-responsivemikto-arm star polymers by RAFT polymerization[J]. Acta PolymericaSinica, 2015(9):1114-1120.
[48] HUERTA E, STALS P J M, MEIJER E W, et al. Consequences offolding a water-soluble polymer around an organocatalyst[J].Angewandte Chemie-International Edition, 2013, 52(10):2906-2910.
[49] SUZUKI N, INOUE T, ASADA T, et al. Asymmetric Aldol reaction onwater using an organocatalyst tethered on a thermoresponsive blockcopolymer[J]. Chemistry Letters, 2013, 42:1493-1495.
[50] LI X J, CHEN M Q, YANG B L, et al. Combining RAFT precipitationpolymerization and surface-initiated RAFT polymerization:anefficient approach to prepare hairy particles-supported proline[J]. RSCAdvances, 2014, 4:43278-43285.
[2] ELMEKAWY A A, SWEENEY J B, BROWN D R. Efficient synthesisof supported proline catalysts for asymmetric aldol reactions[J].Catalysis Science&Technology, 2015, 5:690-696.
[3] HALSKOV K S, DONSLUND B S, PAZ B M, et al. Computationalapproach to diarylprolinol-silyl ethers in aminocatalysis[J]. Accountsof Chemical Research, 2016, 49(5):974-986.
[4] KUMAR T P, BALAJI S V. Sugar amide-pyrrolidine catalyst for theasymmetric Michael addition of ketones to nitroolefins[J]. Tetrahedron:Asymmetry, 2014, 25:473-477.
[5] JORRES M, MERSMANN S, RAABE G, et al. Organocatalyticsolvent-free hydrogen bondingmediated asymmetric Michael additionsunder ball milling conditions[J]. Green Chemistry, 2013, 15:612-616.
[6] CHO E, LEE H, KIM T H. Asymmetric aldol aeaction aatalyzed by L-proline and achiral thiourea fluoroboric acid salt[J]. Bulletin of theKorean Chemical Society, 2015, 36:410-412.
[7] ELMANSY M F, KANG J Y, LINGAMPALLY R, et al. Prolinesulfonamide-catalyzed, domino process for asymmetric synthesis ofamino and hydroxy-substituted bicyclo[2.2.2]octanes[J]. EuropeanJournal of Organic Chemistry, 2016(1):150-157.
[8] LI X J, YANG B L, ZHANG S L, et al. Facile synthesis of hairymicroparticle-/nanoparticle-supported MacMillan and its applicationto Diels-Alder reaction in water[J]. Colloid and Polymer Science,2017, 295:573-582.
[9] RUEPING M, KUENKEL A, TATO F, et al. Asymmetricorganocatalytic domino Michael/Aldol reactions:enantioselectivesynthesis of chiral cycloheptanones, tetrahydrochromenones, andpolyfunctionalized bicyclo-[3.2.1]octanes[J]. Angewandte Chemie-International Edition, 2009, 48:3699-3702.
[10] AN Q J, SHEN J F, BUTT N, et al. Asymmetric domino doubleMichael addition of nitroolefins and aldehyde esters with trans-perhydroindolic acid as an organocatalyst[J]. Synthesis-Stuttgart,2013, 45:1612-1623.
[11] LI X J, ZHANG S L, YANG B L, et al. Magnetic Fe3O4nanoparticlessupporting Macmillan with controlled shell structure as an efficientand reusable catalyst for asymmetric reaction[J]. RSC Advances, 2016,6:86531-86539.
[12] LI J, LI X B, MA S S, et al. An ionic liquid containing L-prolinemoiety as highly efficient and recyclable chiral organocatalyst forMichael addition[J]. Bulletin of the Korean Chemical Society, 2016,37:1259-1264.
[13] ZHANG J L, ZHANG M X, TANG K J, et al. Polymer-based stimuli-responsive recyclable catalytic systems for organic synthesis[J]. Small,2014, 10(1):32-46.
[14] XU Y, HUA Z, ZHANG J, et al. Mimicking enzymatic systems:modulation of the performance of polymeric organocatalysts by ion-specific effects[J]. Chemical Communications, 2016, 52:3392-3395.
[15] NI B K, ZHANG Q Y, DHUNGANA K, et al. Ionic liquid-supported(ILs)(S)-pyrrolidine sulfonamide, a recyclable organocatalyst for thehighly enantioselective Michael addition to nitroolefins[J]. OrganicLetters, 2009, 11(4):1037-1040.
[16] YADAV G D, SINGH S. prolinamide imidazoliumhexafluorophosphate ionic liquid as an efficient reusableorganocatalyst for direct asymmetric aldol reaction in solvent-freecondition[J]. RSC Advances, 2016, 6:100459-100466.
[17] LI X J, LV C N, JIA X B, et al. Nanoparticle based on poly(ionicliquid)as an efficient solid immobilization catalyst for Aldol reactionand multicomponent reaction in water[J]. ACS Applied Materials&Interfaces, 2017, 9:827-835.
[18]汪彩虹,陈硕然,叶常青,等.单分散磁性Fe3O4纳米粒子的研究进展[J].化工进展, 2016, 35(s1):242-247.WANG C H, CHEN S R, YE C Q, et al. Research progress onmonodisperse Fe3O4magnetic nanoparticles[J]. Chemical Industry andEngineering Progress, 2016, 35(s1):242-247.
[19] KHALAFI-NEZHAD A, NOURISEFAT M, PANAHI F. L-proline-modified magnetic nanoparticles(LPMNP):a novel magneticallyseparable organocatalyst[J]. RSC Advances, 2014, 4:22497-22500.
[20] SAFAEI-GHOMI J, AHEDI S. Diastereoselective synthesis ofisoxazolidines and spiroisoxazolidines via catalytic 1, 3-dipolarcycloaddition reactions in the presence of Fe3O4-L-prolinenanoparticles as a magnetic organocatalyst[J]. Tetrahedron Letters, 2016,57:1071-1073.
[21] KUMAR A, DEWAN M, DE A. Aldol condensation in PEG-400catalyzed by recyclable L-proline supported on nano gold surface[J].RSC Advances, 2013, 3:603-607.
[22] ZHAO Y B, ZHANG L W, WU L Y, et al. Silica-supportedpyrrolidine-triazole, an insoluble, recyclable organocatalyst for theenantioselective Michael addition of ketones to nitroalkenes[J].Tetrahedron:Asymmetry, 2008, 19:1352-1355.
[23] RIENTE P, MENDOZA C, PERICAS M A. Functionalization of Fe3O4magnetic nanoparticles for organocatalytic Michael reactions[J].Journal of Materials Chemistry, 2011, 21:7350-7355.
[24] SAFAEI-GHOMI J, ZAHEDI S. L-proline-functionalized Fe3O4nanoparticles as a novel magnetic chiral catalyst for the directasymmetric Mannich reaction[J]. Applied Organometallic Chemistry,2015, 29:566-571.
[25] KONG Y, TAN R, ZHAO L, et al. L-proline supported on ionic liquid-modified magnetic nanoparticles as a highly efficient and reusableorganocatalyst for direct asymmetric aldol reaction in water[J]. GreenChemistry, 2013, 15:2422-2433.
[26] ALZA E, AYALERO S, KASAPLAR P, et al. Polystyrene-supporteddiarylprolinol ethers as highly efficient organocatalysts for michael-type reactions[J]. Chemistry-A European Journal, 2011, 17:11585-11595.
[27] AKAGAWA K, SAKAMOTO S, KUDO K. Direct asymmetric aldolreaction in aqueous media using polymer-supported peptide[J].Tetrahedron Letters, 2005, 46:8185-8187.
[28] ZAYAS H A, LU A, VALADE D, et al. Thermoresponsive polymer-supported L-proline micelle catalysts for the direct asymmetric aldolreaction in water[J]. ACS Macro Letters, 2013, 2:327-331.
[29] HUERTA E, GENABEEK B V, STALS P J M, et al. A modularapproach to introduce function into single-chain polymeric nanoparticles[J]. Rapid Communications in Mass Spectrometry, 2014,35:1320-1325.
[30] LU A, MOATSOU D, HANDS-PORTMAN I, et al. Recyclable L-proline functional nanoreactors with temperature tuned activity basedon core-shell nanogels[J]. ACS Macro Letters, 2014, 3:1235-1239.
[31] LLANES P, SAYALERO S, RODRIGUEZ-ESCRICHA C, et al.Asymmetric cross-and self-aldol reactions of aldehydes in water witha polystyrene-supported triazolylproline organocatalyst[J]. GreenChemistry, 2016, 18:3507-3512.
[32] HE T, LI K, WU M Y, et al. Water promoted enantioselective Aldolreaction by proline cholesterol and-diosgenin based amphiphilicorganocatalysts[J]. Tetrahedron, 2013, 69:5136-5143.
[33] ARIVALAGAN P R, ZHAO Y. Interfacial catalysis of aldol reactionsby prolinamide surfactants in reverse micelles[J]. Organic&Biomolecular Chemistry, 2015, 13:770-775.
[34] LU A, COTANDA P, PATTERSON J P, et al. Aldol reactions catalyzedby L-proline functionalized polymeric nanoreactors in water[J].Chemical Communications, 2012, 48:9699-9701.
[35] LI X J, YANG B L, JIA X B, et al. Temperature-responsive hairyparticle-supported proline for direct asymmetric aldol reaction in water[J]. RSC Advances, 2015, 5:89149-89156.
[36] LU A, MOATSOU D, LONGBOTTOM D A, et al. Tuning the catalyticactivity of L-proline functionalized hydrophobic nanogel particles inwater[J]. Chemical Science, 2013, 4:965-969.
[37]焦彩彬,陈连喜,江杨,等. SiO2/聚合物复合粒子研究进展[J].材料导报A, 2015, 29(6):70-75.JIAO C B, CHEN L X, JIANG Y, et al. Progress of silica/polymercomposite nanoparticles[J]. Materials Review, 2015, 29(6):70-75.
[38] YANG H L, LI S W, WANG X Y, et al. Core-shell silica magneticmicrospheres supported proline as a recyclable organocatalyst for theasymmetric aldol reaction[j]. Journal of Molecular Catalysis A-Chemical, 2012, 364:404-410.
[39] WU T, FENG D D, XIE B, et al. A solution to achieve good reusabilityof MNPs Fe3O4-supported(S)-diphenylprolinoltrimethylsilyl ethercatalysts in asymmetric Michael reactions[J]. RSC Advances, 2016, 6:25246-25254.
[40]徐源鸿,熊兴泉,蔡雷,等.巯基-烯点击化学[J].化学进展, 2012, 24(s1):386-394.XU Y H, XIONG X Q, CAI Lei, et al. Thiol-ene click chemistry[J].Progress in Chemistry, 2012, 24(s1):386-394.
[41]蔡雷,熊兴泉,唐忠科,等.基于巯基-炔的“点击”化学研究进展[J].化工进展, 2011, 30(9):1982-1989.CAI L, XIONG X Q, TANG Z K, et al. Research progress of thiol-yneclick chemistry[J]. Chemical Industry and Engineering Progress, 2011,30(9):1982-1989.
[42] XIA A B, ZHANG C, ZHANG Y P, et al. J?rgensen-Hayashi catalystssupported on poly(ethylene glycol)s as highly efficient and reusableorganocatalysts for the enaminecatalyzed asymmetric Michael reaction[J]. Organic&Biomolecular Chemistry, 2015, 13:9593-9599.
[43] GURYEV A A, ANOKHIN M V, AVERIN A D, et al. Polymer-immobilized aa, aa-bis[bis-3, 5-(trifluoromethyl)phenyl]prolinol silylether:synthesis and application in the asymmetric aa-amination ofaldehydes[J]. Mendeleev Communications, 2015, 25:410-411.
[44] GURYEV A A, ANOKHIN M V, AVERIN A D, et al. HeterogeneousJ?rgensen-Hayashi catalyst for asymmetric Michael addition ofmalonates to a,b-enals. Cooperative effect with Ca(OTf)2[J]. MendeleevCommunications, 2016, 26:469-470.
[45] EVANS A C, LU A, ONDECK C, et al. Organocatalytic tunable aminoacid polymers prepared by controlled radical polymerization[J].Macromolecules, 2010, 43(15):6374-6380.
[46] BOYER C, BULMUS V, PRIYANTO P, et al. The stabilization andbio-functionalization of iron oxide nanoparticles using heterotelechelicpolymers[J]. Journal of Materials Chemistry, 2009, 19:111-123.
[47]吴鹏,申迎华,耿文博,等.多重响应性杂臂星型聚合物的RAFT聚合合成及性能研究[J].高分子学报, 2015(9):1114-1120.WU P, SHEN Y H, GENG W B, et al. Synthesis of multi-responsivemikto-arm star polymers by RAFT polymerization[J]. Acta PolymericaSinica, 2015(9):1114-1120.
[48] HUERTA E, STALS P J M, MEIJER E W, et al. Consequences offolding a water-soluble polymer around an organocatalyst[J].Angewandte Chemie-International Edition, 2013, 52(10):2906-2910.
[49] SUZUKI N, INOUE T, ASADA T, et al. Asymmetric Aldol reaction onwater using an organocatalyst tethered on a thermoresponsive blockcopolymer[J]. Chemistry Letters, 2013, 42:1493-1495.
[50] LI X J, CHEN M Q, YANG B L, et al. Combining RAFT precipitationpolymerization and surface-initiated RAFT polymerization:anefficient approach to prepare hairy particles-supported proline[J]. RSCAdvances, 2014, 4:43278-43285.
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