Новые мультифункциональные органические кислоты Бренстеда как катализаторы реакций образования C-C и C-N связей
![Диссертация: Новые мультифункциональные органические кислоты Бренстеда как катализаторы реакций образования C-C и C-N связей](https://niscu.ru/work/3634835/cover.png)
Y. Belokon, K. Kochetkov, T. Churkina, N. Ikonnikov, S. Orlova, V. Smirnov, A. Chesnokov /Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate/Mendeleev Commun., 1997, 7,137−138. Y. Belokon, K. Kochetkov, T. Churkina, N. Ikonnikov, S. Orlova, V. Smirnov, A. Chesnokov /Asymmetric Michael addition of a glycine synthon to methyl methacrylate… Читать ещё >
Содержание
- I. Введение
- II. Литературный обзор
- 11. 1. Хиральные органические кислоты Бренстеда как катализаторы реакций образования С-С связи
- 11. 1. 1. Производные тиомочевины как катализаторы стереоселективного образования С-С связи
- 11. 1. 2. Применение ТАДДОЛов в асимметрическом органическом катализе
- 11. 1. Хиральные органические кислоты Бренстеда как катализаторы реакций образования С-С связи
- 11. 2. Органический асимметрический катализ реакции триметилсилилциани-рования альдегидов и кетонов
- 11. 3. Энантиоселективная реакция Мукаямы
- 11. 4. Дополнительная активация кислотой Льюиса кислоты Бренседа
- 11. 5. Органокаталитическая энантиоселективная реакция Михаэля
- 11. 6. Использование производных (5)-пролина в асимметрической реакции альдольной конденсации
- IV. 1. Синтез бисСад-ТАДДОЛов
- IV. 2. Изучение каталитической активности бис-ТАДДОЛов в реакции триметилсилилцианирования бензальдегида
- IV. 3. Реакция раскрытия циклогексеноксида различными нуклеофилами, катализируемая металлокомплексными соединениями
Новые мультифункциональные органические кислоты Бренстеда как катализаторы реакций образования C-C и C-N связей (реферат, курсовая, диплом, контрольная)
1. G. Guillena, С. Narjera and D. Ramon /Enantioselective direct aldol reaction: the blossoming of modern organocatalysis/ Tetrahedron: Asymmetry. 2007, 18, 2249−2293.
2. A. Dondoni and A. Massi /Asymmetric Organocatalysis: From Infancy to Adolescence/ Angew. Chem. Int. Ed., 2008, 47, 2−25.
3. Т. Akiyama /Stronger Bronsted Acids/ Chemical Reviews, 2007, Vol. 107, No. 12 5744−5757.
4. T. Akiyama, J. Itoh, and K. Fuchibe /Recent Progress in Chiral Bronsted Acid Catalysis/ Adv. Synth. Catal., 2006, 348, 999 1010.
5. M. S. Sigman, E. N. Jacobsen /Schiff Base Catalysts for the Asymmetric Strecker Reaction Identified and Optimized from Parallel/ J. Am. Chem. Soc. 1998,120, 4901−4902.
6. Petr Vachal and Eric N. Jacobsen /Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction/ J. Am. Chem. Soc., 2002,124, 10 012−10 014.
7. A. Berkessel, F. Cleemann, S. Mukherjee, T. Muller, J. Lex /Highly Efficient Dynamic Kinetic Resolution of Azlactones by Urea-Based Bifiinctional Organocatalysis / Angew. Chem. Int. Ed., 2005, 44, .807−811.
8. Y. Sohtome, Y. Hashimoto, K. Nagasawa /Guanidine-Thiourea Bifunctional Organocatalyst for the Asymmetric Henry (Nitroaldol) Reaction/ Adv. Synth. Catal., 2005, 347, 1643−1648.
9. D. Seebach, A. K. Beck, A. Heckel /TADDOLs, their derivatives, and TADDOL analogues: versatile chiral auxiliaries./ Angew. Chem. Int. Ed., 2001, 40, 92−138.
10. M. Yamaguchi, B. Trost, I. Fleming, S. Schreiber / Lewis Acid Promoted Addition Reactions of Organometallic Compounds/ Comprehensive Organic Synthesis, Vol. 1,. Pergamon Oxford, 1991, 325−353.
11. Y. Belokon, K. Kochetkov, T. Churkina, N. Ikonnikov, S. Orlova, V. Smirnov, A. Chesnokov /Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate/Mendeleev Commun.1997, 7,137−138.
12. N. Momiyama, H. Yamamoto /Acid Catalysis of Achiral Enamine for Regioand Enantioselective Nitroso Aldol Synthesis/ J. Am. Chem. Soc., 2005,127, 1080−1081.
13. Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal /Single enantiomers from a chiral-alcohol catalyst/ Nature, 2003, 424,. 146.
14. A. N. Thadani, A. R. Stankovic, V. H Rawal /Enantioselective Diels-Alder reactions catalyzed by hydrogen bonding/ Proc. Natl. Acad. Sci., 2004,101,. 5846 5850.
15. H. Du, D. Zhao, K. Ding /Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard’s diene and aldehydes by hydrogen-bonding activation: a one-step synthesis of (iSr)-(+)-Dihydrokawain/ Chem. Eur. J., 2004,10,. 5964−5970.
16. X. Zhang, H. Du, Z. Wang, Y. Wu and K. Ding /Experimental and Theoretical Studies on the Hydrogen-Bond-Promoted Enantioselective Hetero-Diels-Alder Reaction of Danishefsky’s Diene with Benzaldehyde/J. Org. Chem., 2006, 71, 2862−2869.
17. J. D. McGilvra, A. K. Unni, K. Modi, V.H. Rawal /Highly Diastereoand Enantioselective Mukaiyama Aldol Reactions Catalyzed by Hydrogen Bonding/ Angew.Chem. Int. Ed., 2006, 45, 6130−6133.
18. N. Momiyama, H. Yamamoto /Bronsted Acid Catalysis of Achiral Enamine for Regio-and Enantioselective Nitroso Aldol Synthesis/ J. Am. Chem. Soc., 2005,127, 1080−1081.
19. K. Tanaka, F. Toda /Solvent-free organic synthesis/ Chem. Rev., 2000, 100, 10 251 074.
20. K. Tanaka, S. Honke, Z. Urbanczyk-Lipkowska, F. Toda /New chiral hosts derived from dimeric tartaric acid: efficient optical resolution of aliphatic alcohols by inclusion complexation/ Eur. J. Org. Chem., 2000, 3171−3176.
21. Y. Belokon, K. Kochetkov, T. Churkina, N. Ikonnikov, S. Orlova, V. Smirnov, A. Chesnokov /Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate/Mendeleev Commun., 1997, 7,137−138.
22. Z Jaszay, G. Nemeth, T. Pham, I. Petnehazy, A. Griin, L. Toke /Catalytic enantioselective Michael addition in the synthesis of a-amonophosphonates/ Tetrahedron: Asymmetry, 2005,16, 3837−3840.
23. K. Matsui, S. Takizawa, H. Sasai /Bifiinctional Organocatalysts for Enantioselective aza-Morita-Baylis-Hillman Reaction/ J. Am. Chem. Soc., 2005,127, 3680−3681.
24. A. Tillman, D. Dixon /An enantioselective Bronsted acid catalyzed enamine Mannich reaction/ Org. Biomol. Chem., 2007, 5, 606−609.
25. S. Lou, P. Moquist, S. Schaus /Asymmetric Allylboration of Ketones Catalyzed by Chiral Diols/ J. Am.Chem. Soc., 2006,128, 12 660−12 661.
26. D. Uraguchi, K. Sorimachi, M. Terada /Organocatalytic Asymmetric Aza-Friedel-Crafts Alkylation ofFuran/ J. Am. Chem. Soc., 2004,126,11 804−11 805.
27. T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe /Enantioselective Mannich-Type Reaction Catalyzed by a Chiral Bransted Acid Derived from TADDOL/ Adv.Synth. Catal., 2005,347, 1523−1526.
28. G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla/Bronsted Acid-Catalyzed Imine Amidation/ J. Am. Chem. Soc., 2005, 127, 1 569 615 697.
29. I. P. Holmes, J. M Brunei /Chemically catalyzed asymmetric cyanohydrin syntheses/ Angew. Chem. Int. Ed., 2004, 43, 2752 2778.
30. Michael North /Synthesis and applications of non-racemic cyanohydrins/ Tetrahedron: Asymmetry, 2003, 14, 147−176.
31. J.-I. Oku, S. Inoue, /Asymmetric cyanohydrin synthesis catalysed by a synthetic cyclic dipeptide/ J. Chem. Soc., Chem. Commun. 1981, 229.
32. D. E. Fuerst, E. N. Jacobsen /Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones//. Am. Chem. Soc, 2005,127, 8964−8965.
33. Stephan J. Zuend and Eric N. Jacobsen /Cooperative Catalysis by Tertiary Amino-Thioureas ?Mechanism and Basis for Enantioselectivity of Ketone Cyanosilylation/. J. Am. Chem. Soc., 2007,129, 15 872−15 883.
34. B. Qin, X. Liu, J. Shi, K. Zheng, H. Zhao, X. Feng /Enantioselective Cyanosilylation of a, aDialkoxy Ketones Catalyzed by Proline-Derived in-Situ-Prepared N-Oxide as Bifunctional Organjcatalyst/ J. Org. Chem., 2007, 72,2374−2378.
35. T. Shi-Kai, D. A. Li /Highly enantioselective chiral Lewis base-catalyzed asymmetric cyanation of ketones/ J. Am. Chem. Soc., 2001,123, 6195−6196.
36. T. Shi-Kai, H. Ran., D. Li /Catalytic asymmetric cyanosilylation of ketones with chiral Lewis base/ J. Am. Chem. Soc., 2003, 125,. 9900−9901.
37. Scott E. Denmark and Won-jin Chung /Lewis Base Catalyzed Addition of Trimethylsilyl Cyanide to Aldehydes/ J. Org. Chem., 2006, 71,4002−4005.
38. Jinhua J. Song, Fabrice Gallou, Jonathan T. Reeves, Zhulin Tan, Nathan K. Yee, and Chris H. Senanayake /Activation of TMSCN by N-Heterocyclic Carbenes for Facile Cyanosilylation of Carbonyl Compounds/ J. Org. Chem., 2006, 71, 1273−1276.
39. Y. Suzuki, A. Bakar, M. K. Muramatsu, M. Sato /Cyanosilylation of aldehydes catalyzed by N-heterocyclic carbenes/ Tetrahedron, 2006, 62, 4227−4231.
40. V. B. Gondi, M. Gravel, V. H. Rawal /Hydrogen Bond Catalyzed Enantioselective Vinylogous Mukaiyama Aldol Reaction/ Org. Lett., 2005; 7 (25) — 5657−5660.
41. T. Hollis, B. Bosnich /Homogeneous Catalysis. Mechanisms of the Catalytic Mukaiyama Aldol and Sakura Allylation Reactions/ J. Am. Chem. Soc., 1995, 7/7, 45 704 581.
42. H. Yamamoto K. Futatsugi /" Designer acids": combined acid catalysis for asymmetric synthesis/ Angew. Chem. Int. Ed., 2005, 44, 1924;1942.
43. K. Ishihara, M. Kaneeda, and H. Yamamoto /Lewis Acid Assisted Chiral Bronsted Acid for Enantioselective Protonation of Silyl Enol Ethers and Ketene Bis (trialkylsilyl) Acetals/ J. Am. Chem. Soc., 1994, 116, 11 179−11 180.
44. K. Ishihara, S. Nakamura, M. Kaneeda, and H. Yamamoto /First Example of a Highly Enantioselective Catalytic Protonation of Silyl Enol Ethers Using a Novel Lewis Acid-Assisted Bransted Acid System/ J. Am. Chem. Soc. 1996,118, 12 854−12 855.
45. K. Mikami, S. Matsukawa /Asymmetric synthesis by enantiomer-selective activation of racemic catalysts / Nature, 1997, 385, 613−615.
46. S. Nakamura, M. Kaneeda, K. Ishihara, H. Yamamoto /Enantioselective Protonation of Silyl Enol Ethers and Ketene Disilyl Acetals with Lewis Acid-Assisted Chiral Br0nsted.
47. J. Wang, H. Li, L. Zu, W. Wang /Enantioselective Organocatalytic Michael Addition Reactions between N-Heterocycles and Nitroolefines/ Org. Lett., 2006; «5 (7) — 1391−1394.
48. T. Ooi, K. Maruoka /Asymmetric Organocatalysis of Structurally Well-Defined Chiral Quaternary Ammonium Fluorides/ Acc. Chem. Res., 2004, 37, 526−533.
49. T. Ooi, D. Ohara, K. Fukumoto, K. Maruoka /Importance of Chiral Phase-Transfer Catalysts with Dual Functions in Obtaining High Enantioselectivity in the Michael Reaction of Malonates and Chalcone Derivatives/ Org. Lett., 2005, Vol. 7 No 15, 31 953 197.
50. B. List, P. Pojarliev, H. J. Martin /Efficient Proline-Catalyzed Michael-Additions of Unmodified Ketones to Nitroolefins/. Org. Lett., 2001, 3, 2423−2425.
51. T. Bui, C. Barbas /A proline-catalyzed asymmetric Robinson annulation reaction./ Tetrahedron Lett., 2000, 41, 6951−6954.
52. J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. Barbas /Catalytic Enantioselective Direct Michael Additions of Ketones to Alkylidene Malonates/ Tetrahedron Lett., 2001, 42, 4441−4444.
53. J. M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, C. F. Barbas /Catalytic direct asymmetric Michael reactions: addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins /Synthesis, 2004, 1509−1521.
54. P. Garcia-Garcia, A. Ladepeche, R. Haider, B. List /Catalytic Asymmetric Michael Reactions of Acetaldehyde/ Angew. Chem. Int. Ed., 2008, 47, 1−4.
55. A. Lattanzi /Enantioselective Michael addition of malonate esters to nitroolefins organocatalyzed by diaryl-2-pyrrolidinemethanols/ Tetrahedron: Asymmetry, 2006, 77, 837−841.
56. Z. G. Hajos, D. R. Parrish /Asymmetric synthesis of bicyclic intermediates of natural product chemistry/ J. Org.Chem., 1974, 39, 1615−1621.
57. U. Eder, G. Sauer, R. Wiechert /New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures/ Angew. Chem., Int. Ed. Engl., 1971,10,496−497.
58. Z. G. Hajos, D. R. Parrish /Asymmetric synthesis of optically active polyciclic organic compounds/ German Patent DE 2 102 623, Jul 29, 1971.
59. U. Eder, G. Sauer, R. Wiechert /Optically active 1,5-indanone and 1,6-naphthalenedione derivatives/ German Patent DE 2 014 757, Oct 7, 1971.
60. Z. G. Hajos /Proline Catalyzed Asymmetric Cyclization. Theory of the Reaction/ Chemistry Preprint Archive, Volume 2002, Issue 9, September 2002, 84−100.
61. C. Agami, J. Levisalles, C. Puchot /A New Diagnostic Tool for Elucidating the Mechanism of Enantioselective Reactions. Application to the Hajos-Parrish Reaction/ J. Chem. Soc., Chem. Comnmn., 1985,441−442.
62. C. Agami, C. Puchot /Kinetic Analysis of the Dual Catalysis by Proline in the Asymmetric Intramolecular Aldol Reaction U. Mol Catal., 1986, 38, 341−343.
63. C. Agami, C. Puchot, H. Sevestre /Is the Mechanism of the Proline-Catalyzed Enantioselective Aldol Reaction Related toBiochemical Processes?/ Tetrahedron Lett., 1986,27, 1501−1504.
64. C. Agami /Mechanism of the Proline-Catalyzed Enantioselective Aldol Reaction/ Recent. Advances. Bull. Soc. Chim. Fr., 1988, 3, 499−507.
65. C. Agami, N. Platzer, H. Sevestre /Enantioselective Cyclizations of Acyclic 1,5-Diketones/Bull. Soc. Chim. Fr., 1987, 2, 358−360.
66. B. List, R. A. Lerner, C. F. Barbas /Proline-Catalyzed Direct Asymmetric Aldol Reactions//. Am. Chem. Soc., 2000,122, 2395−2396.
67. K. Sakthivel, W. Notz, T. Bui, C. F. Barbas /Amino acid catalyzed direct asymmetric aldol reactions: a bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions/ J. Am. Chem. Soc., 2001,123, 5260−5661.
68. B. List /Asymmetric aminocatalysis/ Synlett, 2001,11, 1675−1686.
69. Y. Fu, Z. Li, L. Ding, J. Tao, S. Zhang, M. Tang /Direct asymmetric aldol reaction catalyzed by simple prolinamide phenols/ Tetrahedron: Asimmetry, 17,2006, 3351−3357.
70. A. Russo, G. Botta, A. Lattanzi /Highly stereoselective direct aldol reactions catalyzed by (53-NOBIN-l-prolinamide / Tetrahedron, 2007, 63, 11 886−11 892.
71. X. Xu, Y. Wang, L. Cun, L. Gong /L-Proline amides catalyze direct asymmetric aldol reactions of aldehydes with methylthioacetone and fluoroacetone/ Tetrahedron: Asymmetry, 2007,18, 237−242.
72. V. Maya, M. Raj, V. Singh /Highly Enantioselective Organocatalytic Direct Aldol Reaction in an Aqueous Medium/ Org. Lett., 2007, 9, 13, 2593−2595.
73. M. Gruttadauria, F. Giacalone, A. Marculescu, R. Noto /Novel Prolinamide-Supported Polystyrene as Highly Stereoselective and Recyclable Organocatalyst for the Aldol Reaction/ Adv. Synth. Catal., 2008, 350, 1397−1405.
74. Y. Takemoto, S. Kuraoka, N. Hamaue, К. Aoe, H. Hiramatsu, Ch. Iwata /Enantioselective Cu-catalyzed 1,4-addition of Me3Al to a 4,4-disubstituted cyclohexa-2,5-dienone/ Tetrahedron, 1996, Volume 52, Issue 45, 14 079−14 360.
75. T. Novak, V. Ujj, J. Schindler, M. Czugler, M. Kubinyi, Z. Mayer, E. Fogassy, G. Keglevieh /Resolution of l-Substituted-3-methyl-3-phospholene 1-oxides by Molecular Complex Formation with TADDOL Derivatives/ Tetrahedron: Asymmetry, 2007, 18, 2965−2972.
76. H. Yamashita, T. Mukaiyama /Asymmetric Ring-Opening of cyclohexene Oxide with Various Thiols Catalyzed by Zinc Lq~Tartrate/ Chemistry Letter, 1985, Vol. 14, No. ll, 1643−1646.
77. M. Hayashi, K. Kohmura, N. Oguni /Asymmetric Ring Opening of Symmetrical Epoxides with Trimethylsilyl Azide Using Chiral Titanium Complexes/ Synlett, 1991, 774−777.
78. L. Martinez, J. Leighton, D. Carsten, and E. Jacobsen /Highly Enantioselective Ring Opening of Epoxides Catalyzed by (salen)Cr (III) Complexes/ J. Am. Chem. Soc., 1995, 117,. 5897−5898.
79. Xue-Long Hou, Jie Wu, Li-Xin Dai, Li-Jun Xia, Ming-Hua Tan /Desymmetric ring-opening of meso-Qpoxides with anilines: a simple way to chiral p-amino alcoholsg/ Tetrahdron: Asymmetry, 1998, 9, 1747−1752.
80. S. Sagawa, H. Abe, Y. Hase, T. Inaba /Catalytic Asymmetric Aminolysis of 3,5,8-Trioxabicyclo5.1.0.octane Providing an Optically Pure 2-Amino-l, 3,4-butanetriol Equivalent/ J. Org. Chem., 1999, 64,4962−4965.
81. C. Schneider, A. Sreekanth, E. Mai /Scandium-Bipyridine-Catalyzed Enantioselective Addition of Alcohols and Amines to meso-Epoxides/ Angew. Chem. Int. Ed., 2004, 43, 5691−5694.
82. S. Azoulay, K. Manabe, and S. Kobayashi /Catalytic Asymmetric Ring Opening of w&yo-Epoxides with Aromatic Amines in Water/ Org. Lett., 2005, 7, 4593−4595.
83. C. Ogawa, S. Azoulay, S. Kobayashi /For a Bi (OTf)3-bipyridine-catalyzed aminolysis of weso-epoxide/ Heterocycles, 2006, 66, 201.
84. B. Gao, Y. Wen, Z. Yang, X. Huang, X. Liu, X. Feng /Asymmetric Ring Opening of /weso-Epoxides with Aromatic Amines Catalyzed by a New Proline-BasedDioxideIndium Tris (triflate) Complex/ Adv. Synth. CataL, 2008, 350, 385−390.
85. B. Cole, K. Shimizu, C. Krueger, J. Harrity, M. Snapper, A. Hoveyda /Discovery of Chiral Catalysts through Ligand Diversity: Ti-Catalyzed Enantioselective Addition of TMSCN to meso Epoxides/ Angew. Chem. Int. Ed., 1996, 35, 1668−1671.
86. S. Schaus and E. Jacobsen /Asymmetric Ring Opening of Meso Epoxides with TMSCN Catalyzed by (pybox)lanthanide Complexes/ Org. Lett., 2000, 2, 1001−1004.
87. A. G. Carel, M. Weijers /.Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides by Rhodotorula glutinisi Tetrahedron: Asymmetry, 1997, 8, 639−647 '.
88. S. Fukuzuni, K. Ohkudo /Fluorescence Maxima of 10-Methylacridone-Metal Ion Salt Complexes: A Convenient and Quantitative Measure of Lewis Acidity of Metal Ion Salts/ J. Am. Chem. Soc., 2002,124, 10 270−10 271.
89. A. Casaschi, G. Desimoni, G. Faita, A. G. Invernizzi, S. Lanati, and P. Righetti /Catalysis with inorganic cations. 2. The effect of some perchlorates on Diels-Alder reaction rates/ J. Am. Chem. Soc., 1993,115, 8002−8007.
90. A. N. Pushin, S. E. Tkachewko, L. V. MartynovDoklady Akademii Nauk SSSR, 1988,299, 154.
91. G. Desimoni, G. Faita, P.P. Righetti, G. Tacconi /Lithium Perchlorate Catalysis of the Hetero Diels-Alder Reaction: a Specific Lithium Cation Effect / Tetrahedron, 1991, 47, 8399−8406.
92. M. Reetz, B. Raguse, C. Marth, H. Hugel, T. Bach, D. Fox /A Rapid Injection NMR Study of the Chelation Controlled Mukaiyama Aldol Addition: TiCl4 Versus LiC104 as the Lewis Acid /Tetrahedron, 1992, 48, 5731−5742.