近年来脯氨酸及其衍生物催化的不对称有机反应受到了广泛关注,将其负载于载体上使用也引起了人们的极大兴趣.负载方式大致分为3种:共价键负载,离子对结合或物理吸附等作用负载,以及在离子液体中的两相催化剂.本文对近年来出现的负载脯氨酸及其衍生物催化的不对称反应(Aldol反应、Michael加成反应)研究进展进行了综述.
参考文献
[1] | Guillena G;Najera C;Ramon D J .[J].TETRAHEDRON-ASYMMETRY,2007,18:2249. |
[2] | Pellissier H .[J].Tetrahedron,2007,63:9267. |
[3] | Guillena G;Ramon DJ .Enantioselective alpha-heterofunctionalisation of carbonyl compounds: organocatalysis is the simplest approach[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2006(10):1465-1492. |
[4] | Dalko P I;Moisan L .[J].Angewandte Chemie International Edition,2004,43:5138. |
[5] | List B .[J].Chemical Reviews,2007,107:5413. |
[6] | Houk K N;List B .[J].Accounts of Chemical Research,2004,37:487. |
[7] | Ibrahem I;Zou WB;Casas J;Sunden H;Cordova A .Direct organocatalytic enantioselective alpha-aminomethylation of ketones[J].Tetrahedron,2006(2/3):357-364. |
[8] | Hajos Z G;Parrish D R .[P].DE 2 102 623,1971. |
[9] | Hajos Z G;Parrish D R .[J].Journal of Organic Chemistry,1974,39:1615. |
[10] | Eder U;Wiechert R;Sauer G .[P].DE 2014757,1971. |
[11] | Eder U;Sauer G;Wiechert R .[J].Angewandte Chemie International Edition,1971,10:496. |
[12] | List B.;Barbas CF.;Lerner RA. .Proline-catalyzed direct asymmetric aldol reactions[J].Journal of the American Chemical Society,2000(10):2395-2396. |
[13] | List B .[J].Tetrahedron,2002,58:5573. |
[14] | Jarvo E R;Miller S J .[J].Tetrahedron,2002,58:2481. |
[15] | Notz W;Tanaka F;Barbas C F III .[J].Accounts of Chemical Research,2004,37:580. |
[16] | 郑欣,王永梅.脯氨酸催化的不对称有机反应[J].化学进展,2008(11):1675-1686. |
[17] | 李经纬,徐利文,夏春谷.脯氨酸催化剂在不对称反应中的研究进展[J].有机化学,2004(01):23-28. |
[18] | Sakthivel K;Notz W;Bui T;Barbas C F III .[J].Journal of the American Chemical Society,2001,123:5260. |
[19] | Suri J T;Mitsumori S;Albertshofer K;Tanaka F Barbas C F III .[J].Journal of Organic Chemistry,2006,71:3822. |
[20] | Grondaland C;Enders D .[J].Tetrahedron,2006,62:329. |
[21] | Suri J T;Ramachary D B;Barbas C F III .[J].Organic Letters,2005,7:1383. |
[22] | Ibrahem I;Cordova A .[J].Tetrahedron Letters,2005,46:3363. |
[23] | Storer RI;MacMillan DWC .Enantioselective organocatalytic aldehyde-aldehyde cross-aldol couplings. The broad utility of alpha-thioacetal aldehydes[J].Tetrahedron,2004(35):7705-7714. |
[24] | Casas J;Sunden H;Cordova A .[J].Tetrahedron Letters,2004,45:6117. |
[25] | Pan Q;Zou B;Wang Y;Ma D .[J].Organic Letters,2004,6:1009. |
[26] | Northrup A B;Mangion I K;Hettche F;MacMillan D W C .[J].Angewandte Chemie International Edition,2004,43:2152. |
[27] | Allemann C;Gordillo R;Clemente F R;Cheong P H Y Houk K N .[J].Accounts of Chemical Research,2004,37:558. |
[28] | Thayumanavan R;Tanaka F;Barbas C F III .[J].Organic Letters,2004,6:3541. |
[29] | Pidathala C;Hoang L;Vignola N;List B .[J].Angewandte Chemie International Edition,2003,42:2785. |
[30] | Giacalone, F.;Gruttadauria, M.;Agrigento, P.;Lo Meo, P.;Noto, R. .Advances towards highly active and stereoselective simple and cheap proline-based organocatalysts[J].European journal of organic chemistry,2010(29):5696-5704. |
[31] | An, Y.-J.;Zhang, Y.-X.;Wu, Y.;Liu, Z.-M.;Pi, C.;Tao, J.-C. .Simple amphiphilic isosteviol-proline conjugates as chiral catalysts for the direct asymmetric aldol reaction in the presence of water[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2010(6):688-694. |
[32] | Bui T;Barbas C F III .[J].Tetrahedron Letters,2000,41:6951. |
[33] | List B. .The direct catalytic asymmetric three-component Mannich reaction[J].Journal of the American Chemical Society,2000(38):9336-9337. |
[34] | Cordova A;Notz W;Zhong G;Betancort J M Barbas C F III .[J].Journal of the American Chemical Society,2002,124:1842. |
[35] | List B.;Pojarliev P.;Biller WT.;Martin HJ. .The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols[J].Journal of the American Chemical Society,2002(5):827-833. |
[36] | Notz W.;Tanaka F.;Watanabe S.;Chowdari NS.;Turner JM.;Thayumanavan R. Barbas CF. .The direct organocatalytic asymmetric Mannich reaction: Unmodified aldehydes as nucleophiles [Review][J].The Journal of Organic Chemistry,2003(25):9624-9634. |
[37] | Chowdari N S;Suri J T;Barbas C F III .[J].Organic Letters,2004,6:2507. |
[38] | Hayashi Y;Tsuboi W;Ashimine I;Urushima T,Shoji M,Sakai K .[J].Angewandte Chemie International Edition,2003,42:3677. |
[39] | Cordova A. .One-pot organocatalytic direct asymmetric synthesis of gamma-amino alcohol derivatives[J].Synlett,2003(11):1651-1654. |
[40] | List B;Pojarliev P;Martin H J .[J].Organic Letters,2001,3:2423. |
[41] | Betancort J M;Barbas C F III .[J].Organic Letters,2001,3:3737. |
[42] | Enders D.;Seki A. .Proline-catalyzed enantioselective Michael additions of ketones to nitrostyrene[J].Synlett,2002(1):26-28. |
[43] | Gryko D .Organocatalytic transformation of 1,3-diketones into optically active cyclohexanones[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2005(7):1377-1383. |
[44] | Mangion I K;MacMillan D W C .[J].Journal of the American Chemical Society,2005,127:3696. |
[45] | B(o)gevig A;Juhl K;Kumaragurubaran N;Zhuang W,J(o)rgensen K N .[J].Angewandte Chemie International Edition,2002,41:1790. |
[46] | List B .[J].Journal of the American Chemical Society,2002,124:5656. |
[47] | Suri JT;Steiner DD;Barbas CF .Organocatalytic enantioselective synthesis of metabotropic glutamate receptor ligands[J].Organic letters,2005(18):3885-3888. |
[48] | Sabitha G;Fatima N;Reddy E V;Yadav J S .[J].Advanced Synthesis and Catalysis,2005,347:1353. |
[49] | Thayumanavan R;Dhevalapally B;Sakthivel K;Tanaka F Barbas C F III .[J].Tetrahedron Letters,2002,43:3817. |
[50] | Ramachary D B;Chowdari N S;Barbas C F III .[J].Tetrahedron Letters,2002,43:6743. |
[51] | Shi M;Jiang J K;Li C Q .[J].Tetrahedron Letters,2002,43:127. |
[52] | Chen S H;Hong B C;Su C F;Sarshar S .[J].Tetrahedron Letters,2005,46:8899. |
[53] | Imbriglio J E;Vasbinder M M;Miller S J .[J].Organic Letters,2003,5:3741. |
[54] | Cozzi F .Immobilization of organic catalysts: When, why, and how[J].Advanced synthesis & catalysis,2006(12/13):1367-1390. |
[55] | Benaglia M;Pugliesi A;Cozzi F .[J].Chemical Reviews,2003,103:3401. |
[56] | Corma A;Garcia H .Silica-bound homogenous catalysts as recoverable and reusable catalysts in organic synthesis[J].Advanced synthesis & catalysis,2006(12/13):1391-1412. |
[57] | Benaglia M .[J].New Journal of Chemistry,2006,30:1525. |
[58] | Benaglia M;Celentano G;Cozzi F .[J].Advanced Synthesis and Catalysis,2001,343:171. |
[59] | Benaglia M;Cinquini M;Cozzi F;Puglisi A Celentano G .[J].Advanced Synthesis and Catalysis,2002,344:533. |
[60] | Kondo K;Yamano T;Takemoto K .[J].Makromolekulare Chemie,1985,186:1781. |
[61] | Font D;Jimeno C;Pericas MA .Polystyrene-supported hydroxyproline: An insoluble, recyclable organocatalyst for the asymmetric aldol reaction in water[J].Organic letters,2006(20):4653-4655. |
[62] | Font D;Sayalero S;Bastero A;Jimeno C;Pericas MA .Toward an artificial aldolase[J].Organic letters,2008(2):337-340. |
[63] | Giacalone F;Gruttadauria M;Mossuto-Marculescu A;Noto R .[J].Tetrahedron Letters,2007,48:255. |
[64] | Gruttadauria M;Giacalone F;Marculescu AM;Lo Meo P;Riela S;Noto R .Hydrophobically directed aldol reactions: Polystyrene-supported l-proline as a recyclable catalyst for direct asymmetric aldol reactions in the presence of water[J].European journal of organic chemistry,2007(28):4688-4698. |
[65] | Liu YX;Sun YN;Tan HH;Liu W;Tao JC .Linear polystyrene anchored L-proline, new recyclable organocatalysts for the aldol reaction in the presence of water[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2007(22):2649-2656. |
[66] | Liu Y X;Sun Y N;Tan H H;Tao J C .[J].Catalysis Letters,2008,120:281. |
[67] | Dhar D;Beadham I;Chandrasekaran S .[J].Proceedings of the Indian Academy of Science:Chemical Sciences,2003,115:365. |
[68] | Calderón F;Fernández R;Sánchez F;Femández-Mayoralas A .[J].Advanced Synthesis and Catalysis,2005,347:1395. |
[69] | Doyagüez E G;Calderón F;Sánchez F;FernándezMayoralas A .[J].Journal of Organic Chemistry,2007,72:9353. |
[70] | Kotrusz P;Kmentová I;Gotov B;Toma (S),Sol(c)ániová E.[J].Chemical Communications,2002:2510. |
[71] | Loh T P;Feng L C;Yang H Y;Yang J Y .[J].Tetrahedron Letters,2002,43:8741. |
[72] | Cordova A .[J].Tetrahedron Letters,2004,45:3949. |
[73] | Gruttadauria M;Riela S;Lo Meo P;D'Arma F Noto R .[J].Tetrahedron Letters,2004,45:6113. |
[74] | Gruttadauria M;Riela S;Aprile C;Lo Meo P;D'Anna F;Noto R .Supported ionic liquids. New recyclable materials for the L-proline-catalyzed aldol reaction[J].Advanced synthesis & catalysis,2006(1/2):82-92. |
[75] | Aprile C;Giacalone F;Gruttadauria M;Marculescu AM;Noto R;Revell JD;Wennemers H .New ionic liquid-modified silica gels as recyclable materials for L-prolineor H-Pro-Pro-Asp-NH2-catalyzed aldol reaction[J].Green chemistry,2007(12):1328-1334. |
[76] | Miao W;Chan T H .[J].Advanced Synthesis and Catalysis,2006,348:1711. |
[77] | Zhou L;Wang L .[J].Chemistry Letters,2007,36:628. |
[78] | Lombardo M;Pasi F;Easwar S;Trombini C .[J].Advanced Synthesis and Catalysis,2007,349:2061. |
[79] | Siyutkin D E;Kucherenko A S;Struchkova M I;Zlotin S G .[J].Tetrahedron Letters,2008,49:1212. |
[80] | Kucherenko AS;Struchkova MI;Zlotin SG .The (S)-proline/polyelectrolyte system: An efficient, heterogeneous, reusable catalyst for direct asymmetric aldol reactions[J].European journal of organic chemistry,2006(8):2000-2004. |
[81] | Hu S;Jiang T;Zhang Z;Zhu A Han B Song J Xie Y Li W .[J].Tetrahedron Letters,2007,48:5613. |
[82] | Bellis E;Kokotos G .[J].Journal of Molecular Catalysis A:Chemical,2005,241:166. |
[83] | Kehat T;Portnoy M.[J].Chemical Communications,2007:2823. |
[84] | Shen Z;Ma J;Liu Y;Jiao C Li M Zhang Y .[J].Chirality,2005,17:556. |
[85] | Liu K;Haeussinger D;Woggon WD .Aldol reactions in water using a beta-cyclodextrin-binding proline derivative[J].Synlett,2007(14):2298-2300. |
[86] | Huang J;Zhang X;Armstrong D W .[J].Angewandte Chemie International Edition,2007,46:9073. |
[87] | Kristensen, TE;Vestli, K;Fredriksen, KA;Hansen, FK;Hansen, T .Synthesis of Acrylic Polymer Beads for Solid-Supported Proline-Derived Organocatalysts[J].Organic letters,2009(14):2968-2971. |
[88] | Tang Z;Jiang F;Yu L T;Cui X Gong L Z Mi A Q Jiang Y Z Wu Y D .[J].Journal of the American Chemical Society,2003,125:5262. |
[89] | Guo HM;Cun LF;Gong LZ;Mi AQ;Jiang YZ .Asymmetric direct aldol reaction catalyzed by an L-prolinamide derivative: considerable improvement of the catalytic efficiency in the ionic liquid[J].Chemical communications,2005(11):1450-1452. |
[90] | Andreae MRM;Davis AP .Heterogeneous catalysis of the asymmetric aldol reaction by solid-supported proline-terminated peptides[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2005(14):2487-2492. |
[91] | Akagawa K;Sakamoto S;Kudo K .[J].Tetrahedron Letters,2005,46:8185. |
[92] | Krattiger P;Kovasy R;Revell J D;Ivan S Wennemers H .[J].Organic Letters,2005,7:1101. |
[93] | Revell JD;Gantenbein D;Krattiger P;Wennemers H .Solid-supported and pegylated H-Pro-Pro-Asp-NHR as catalysts for asymmetric aldol reactions[J].Biopolymers: Original Research on Biomolecules and Biomolecular Assemblies,2006(1):105-113. |
[94] | Kofoed J;Darbre T;Reymond JL .Artificial aldolases from peptide dendrimer combinatorial libraries[J].Organic & biomolecular chemistry,2006(17):3268-3281. |
[95] | Yan J C;Wang L .[J].Synthesis,2008,13:2065. |
[96] | Siyutkin, DE;Kucherenko, AS;Zlotin, SG .A new (S)-prolinamide modified by an ionic liquid moiety-a high performance recoverable catalyst for asymmetric aldol reactions in aqueous media[J].Tetrahedron,2010(2):513-518. |
[97] | Zou, J.;Zhao, W.;Li, R.;Zhang, H.;Cui, Y. .Synthesis of PVC-TEPA-supported proline derivative and its catalytic behavior in the direct asymmetric aldol reaction[J].Journal of Applied Polymer Science,2010(2):1020-1026. |
[98] | Wu Y;Zhang Y;Yu M;Zhao G Wang S .[J].Organic Letters,2006,g:4417. |
[99] | Luo S;Li J;Xu H;Zhang L Cheng J P .[J].Organic Letters,2007,9:3675. |
[100] | Li J;Hu S;Luo S;Cheng J P.[J].European Journal of Organic Chemistry,2009:132. |
[101] | Luo S;Mi X;Zhang L;Liu S Xu H Cheng J P .[J].Tetrahedron,2007,63:1923. |
[102] | Gao Q;Lu S M;Liu Y;Li C .[J].Tetrahedron Letters,2011,52:3779. |
[103] | Li, J.;Yang, G.;Qin, Y.;Yang, X.;Cui, Y. .Recyclable Merrifield resin-supported thiourea organocatalysts derived from l-proline for direct asymmetric aldol reaction[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2011(6):613-618. |
[104] | Benaglia M.;Cinquini M.;Cozzi F.;Puglisi A.;Celentano G. .Poly(ethylene-glycol)-supported proline: a recyclable aminocatalyst for the enantioselective synthesis of gamma-nitroketones by conjugate addition[J].Journal of molecular catalysis, A. Chemical,2003(0):157-163. |
[105] | Gu L;Wu Y;Zhang Y;Zhao G .[J].Journal of Molecular Catalysis A:Chemical,2007,263:186. |
[106] | Kotrusz P;Alemayehu S;Toma S;Schmalz H G,Adler A.[J].European Journal of Organic Chemistry,2004:1577. |
[107] | Kotrusz P;Toma S .[J].MOLECULES,2006,11:197. |
[108] | Meciarova M;Toma S;Kotrusz P .Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts[J].Organic & biomolecular chemistry,2006(7):1420-1424. |
[109] | Alza E;Cambeiro XC;Jimeno C;Pericas MA .Highly enantioselective Michael additions in water catalyzed by a PS-Supported pyrrolidine[J].Organic letters,2007(19):3717-3720. |
[110] | Luo S;Li J;Zhang L;Xu H Cheng J P .[J].Chemistry-A European Journal,2008,14:273. |
[111] | Liu, J;Li, PH;Zhang, YC;Ren, K;Wang, L;Wang, GW .Recyclable Merrifield Resin-Supported Organocatalysts Containing Pyrrolidine Unit through A(3)-Coupling Reaction Linkage for Asymmetric Michael Addition[J].Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry,2010(4):432-441. |
[112] | Li Y;Liu X Y;Zhao G .[J].TETRAHEDRON-ASYMMETRY,2006,17:2034. |
[113] | Alza E;Pericàs M A .[J].Advanced Synthesis and Catalysis,2009,351:3051. |
[114] | Chuan Y M;Chen G H;Peng Y G .[J].Tetrahedron Letters,2009,50:3054. |
[115] | Luo S;Mi X;Zhang L;Liu S,Xu H,Cheng J P .[J].Angewandte Chemie International Edition,2006,45:3093. |
[116] | Wu LY;Yan ZY;Xie YX;Niu YN;Liang YM .Ionic-liquid-supported organocatalyst for the enantioselective Michael addition of ketones to nitroolefins[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2007(17):2086-2090. |
[117] | Ni B;Zhang Q;Headley A D .[J].Green Chemistry,2007,9:737. |
[118] | Xu, D.-Z.;Liu, Y.;Shi, S.;Wang, Y. .Chiral quaternary alkylammonium ionic liquid [Pro-dabco][BF_4]: As a recyclable and highly efficient organocatalyst for asymmetric Michael addition reactions[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2010(20):2530-2534. |
[119] | Chowdari NS.;Ramachary DB.;Barbas CIII. .Organocatalysis in ionic liquids: Highly efficient L-proline-catalyzed direct asymmetric Mannich reactions involving ketone and aldehyde nucleophiles[J].Synlett,2003(12):1906-1909. |
[120] | Liu B;Xu D;Dong J;Yang H Zhao D Luo S Xu Z .[J].Synthetic Communications,2007,37:3003. |
[121] | Huang K;Huang Z Z;Li X L .[J].Journal of Organic Chemistry,2006,71:8320. |
[122] | Guo HM;Niu HY;Xue MX;Guo QX;Cun LF;Mi AQ;Jiang YZ;Wang JJ .L-Proline in an ionic liquid as an efficient and reusable catalyst for direct asymmetric alpha-aminoxylation of aldehydes and ketones[J].Green chemistry,2006(8):682-684. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%