Asymmetric catalysis on solids

Current Opinion in Solid State and Materials Science

Volumn 4, Issue 1, 1999, Pages 85-96

  Bein, Thomas ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002224467     PISSN: 13590286     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-0286(99)80016-3     Document Type: Article

References (95)

1. Noyori R: Asymmetric Catalysis in Organic Synthesis. New York: Wiley & Sons; 1994.
2. Wells PB, Wilkinson AG: Platinum group metals as heterogeneous enantioselective catalysts. Topics Catal 1998, 5:39-50. One of a few excellent reviews [2-10] with an emphasis on chirally modified metal catalysis.
3. Kulkarni SJ: Recent trends in applications of zeolites and molecular sieves for synthesis of speciality and fine chemicals. Stud Surf Sci Catal 1998, 113:151-161. See annotation [2].
4. Blaser H-U, Pugin B: Scope and limitations of heterogeneous enantioselective catalysts. Spec Publ - R Soc Chem 1998, 216:101-109. See annotation [2].
5. Baiker A: Chiral catalysis on solids. Curr Opin Solid State Mater Sci 1998, 3:86-93. See annotation [2].
6. Hutchings G, Page P, Hancock F: Catalysts for change. Chem Brit 1997, 33:46-48. See annotation [2].
7. Baiker A: Progress in asymmetric heterogeneous catalysis: design of novel chirally modified platinum metal catalysts. J Mol Catal A 1997, 115:473-493. See annotation [2].
8. Blaser HU, Jalett HP, Muller M, Studer M: Enantioselective hydrogenation of alpha-ketoesters using cinchona modified platinum catalysts and related systems: a review. Catal Today 1997, 37:441-463. See annotation [2].
9. Osawa T, Harada T, Tai A: Enantio-differentiating hydrogenation of prochiral ketones over modified nickel. Catal Today 1997, 37:465-480. See annotation [2].
10. Sun Y, Wang J, LeBlond C, Landau RN, Laquidara J, Sowa, John R Jr, Blackmond DG: Kinetic influences on enantioselectivity in asymmetric catalytic hydrogenation. J Mol Catal A: Chem 1997, 115:495-502. See annotation [2].
11. Augustine RL, Tanielyan SK: Enantioselective heterogeneous catalysis. 3. Effect of oxygen on catalyst activity and selectivity in the enantioselective hydrogenation of pyruvates. J Mol Catal A: Chem 1997, 118:79-87.
12. 3 catalyst. J Catal 1998, 173:282-294. Detailed kinetic study of the hydrogenation of ethyl pyruvate over a dihydrocinchonidine-modified supported Pt catalyst.
13. Torok B, Felfoldi K, Szakonyi G, Balazsik K, Bartok M: Enantiodifferentiation in asymmetric sonochemical hydrogenations. Catal Lett 1998, 52:81-84.
14. Schürch M, Heinz T, Aeschimann R, Mallat T, Pfaltz A, Baiker A: Design of new modifiers for the enantioselective hydrogenation of ethyl pyruvate. J Catal 1998, 173:187-195. A systematic study on the effects of new modifiers, including 1-(9-anthracenyl)-2-(1-pyrrolidinyl)ethanol, for Pt in the enantioselective hydrogenation of ethyl pyruvate.
15. Tungler A, Mathe T, Tarnai T, Fodor K, Toth G, Kajtar J, Kolossvary I, Herenyi B, Sheldon RA: (-)-Dihydroapovincaminic acid ethyl ester, preparation and use as a chiral modifier in enantioselective heterogeneous catalytic hydrogenations. Tetrahedron: Asymmetry 1995, 6:2395-2402.
16. Tungler A, Tarnai T, Mathe T, Vidra G, Petro J, Sheldon RA: New asymmetric heterogeneous catalytic hydrogenation reactions. Chem Ind 1995, 62:201-212.
17. Zhang HB, Zhang J, Fu RN, Zuo XB, Liu HF: High-resolution GC separation of alkyl lactate enantiomers and the determination of the enantiomeric excess of the optical isomers of alkyl lactates. Chromatographia 1998, 48:305-309.
18. Taoufik M, Santini C, Basset JM, Candy JP: Grafting of chiral derivatives of germanium on metallic surfaces. Formation of asymmetric heterogeneous catalysts by surface organometallic chemistry. J Chim Phys Phys-Chim Biol 1997, 94:1969-1974.
19. Smith GV, Cheng J, Song R: New enantioselective heterogeneous catalysts. Catal Lett 1997, 45:73-78.
20. Keane MA: Interaction of optically active tartaric acid with a nickel-silica catalyst: role of both the modification and reaction media in determining enantioselectivity. Langmuir 1997, 13:41-50.
21. 2 was investigated in a detailed kinetic study. The modifier also enhanced the rate of hydrogenation.
22. Bayston DJ, Travers CB, Polywka MEC: Synthesis and evaluation of a chiral heterogeneous transfer hydrogenation catalyst. Tetrahedron: Asymmetry 1998, 9:2015-2018.
23. Torok B, Wolfling J, Schneider G, Bartok M: Homogeneous and heterogeneous asymmetric reactions. Part IX. Asymmetric transfer hydrogenation of 16-methyl-substituted steroid 17-ketones in the presence of rhodium(1) complexes. React Kinet Catal Lett 1998, 64:35-40.
24. Kolb HC, Vannieuwenhze MS, Sharpless KB: Catalytic asymmetric dihydroxylation. Chem Rev 1994, 94:2483-2547.
25. Song CE, Yang JW, Ha HJ, Lee SG: Efficient and practical polymeric catalysts for heterogeneous asymmetric dihydroxylation of olefins. Tetrahedron: Asymmetry 1996, 7:645-648.
26. Nandanan E, Sudalai A, Ravindranathan T: New polymer supported cinchona alkaloids for heterogeneous catalytic asymmetric dihydroxylation of olefins. Tetrahedron Lett 1997, 38:2577-2580.
27. Canali L, Song CE, Sherrington DC: Polymer-supported biscinchona alkaloid ligands for asymmetric dihydroxylation of alkenes - a cautionary tale. Tetrahedron: Asymmetry 1998, 9:1029-1034.
28. Bolm C, Gerlach A: Polymer-supported catalytic asymmetric sharpless dihydroxylations of olefins. Eur J Org Chem 1998:21-27. The authors discuss two important methods for alkaloid ligand recovery in asymmetric dihydroxylation of olefins: covalent attachment to supports, and anchoring to soluble polymers that are recovered by precipitation.
29. Karjalainen JK, Hormi OEO, Sherrington DC: Heterogeneous asymmetric epoxidation of cis allylic alcohols: Use of polymer-supported Ti(IV) catalysts. Tetrahedron: Asymmetry 1998, 9:2019-2022.
30. Canali L, Karjalainen JK, Sherrington DC, Hormi O: Efficient polymer-supported sharpless alkene epoxidation catalyst. Chem Commun 1997:123-124.
31. Irurre J, Fernandez-Serrat A, Rosanas F: Polymer-supported chiral diol as ligand of Ti(IV) for enantioselective Diels-Alder reaction. Chirality 1997, 9:191-197.
32. 2Zn addition mediated by a polymer-incorporated titanate. Helv Chim Acta 1997, 80:2027-2032. TADDOL ligands for titanate were modified with dendritic branches attached to their aryl groups and used as cross-linkers in a polymerization, resulting in enantioselective polymer catalysts.
33. Rheiner PB, Seebach D: High-molecular-weight and polymer-bound dendritic TADDOLs for membrane reactors and heterogeneous enantioselective Lewis acid catalysis. Polym Mater Sci Eng 1997, 77:130-131.
34. Altava B, Burguete MI, Fraile JM, Garcia JI, Luis SV, Mayoral JA, Royo AJ, Salvador RV: Polymer-supported Al and Ti species as catalysts for Diels-Alder reactions. Studies Surf Sci Catal 1997, 108:509-516.
35. Fraile JM, Mayoral JA, Royo AJ, Salvador RV, Altava B, Luis SV, Burguete MI: Supported chiral amino alcohols and diols functionalized with aluminum and titanium as catalysts of Diels-Alder reaction. Tetrahedron 1996, 52:9853-9862.
36. Soai K, Hayase T: Asymmetric-synthesis using N,N-dialkylnorephedrines and pyrrolidinylmethanol derivatives as chiral catalysts and ligands. J Synth Org Chem Jpn 1995, 53:138-150.
37. Wei Z, Loebach JL, Wilson SR, Jacobsen EN: Enantioselective epoxidation of unfunctionalized olefins catalyzed by (salen)-manganese complexes. J Am Chem Soc 1990, 112:2801-2803.
38. Minutolo F, Pini D, Petri A, Salvadori P: Heterogeneous asymmetric epoxidation of unfunctionalized olefins catalyzed by polymer-bound (salen-manganese complexes. Tetrahedron: Asymmetry 1996, 7:2293-2302.
39. Minutolo F, Pini D, Salvadori P: Polymer-bound chiral (salen)Mn(III) complex as heterogeneous catalyst in rapid and clean enantioselective epoxidation of unfunctionalized olefins. Tetrahedron Lett 1996, 37:3375-3378.
40. Shimizu KD, Snapper ML, Hoveyda AH: High-throughput strategies for the discovery of catalysts. Chem Eur J 1998, 4:1885-1889.
41. Francis MB, Jamison TF, Jacobsen EN: Combinatorial libraries of transition-metal complexes, catalysts and materials. Curr Opin Chem Biol 1998, 2:422-428.
42. Cole BM, Shimizu KD, Krueger CA, Harrity JPA, Snapper ML, Hoveyda AH: Discovery of chiral catalysts through ligand diversity: Ti-catalyzed enantioselective addition of TMSCN to meso epoxides. Angew Chem Int Ed Engl 1996, 35:1668-1671.
43. Shimizu KD, Cole BM, Krueger CA, Kuntz KW, Snapper ML, Hoveyda AH: Search for chiral catalysts through ligand diversity: substrate-specific catalysts and ligand screening on solid phase. Angew Chem Int Ed Engl 1997, 36:1704-1707. Combinatorial methods for catalyst construction on polymer beads were used to create optimized Schiff base type ligands for the titanium catalyzed enantioselective addition of trimethylsilylcyanide to epoxides.
44. Sigman MS, Jacobsen EN: Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries. J Am Chem Soc 1998, 120:4901-4902. The authors demonstrate the use of combinatorial techniques for the synthesis of Schiff base type catalysts on polymer beads, for the asymmetric hydrocyanation of imines.
45. Vankelecom IFJ, Tas D, Parton RF, Van de Vyver V, Jacobs PA: Chiral catalytic membranes. Angew Chem Int Ed Engl 1996, 35:1346-1348.
46. Vankelecom IFJ, Vercruysse KAL, Neys PE, Tas DWA, Janssen KBM, Knops-Gerrits PP, Jacobs PA: Novel catalytic membranes for selective reactions. Topics Catal 1998, 5:125-132. An overview of recent developments in the design of catalytic polymer membranes by occlusion of molecular catalysts.
47. Tas D, Thoelen C, Vankelecom IFJ, Jacobs PA: Bifunctional catalytic membrane containing Bronsted acids and sites for enantioselective hydrogenation. Chem Commun 1997:2323-2324.
48. Janssen KBM, Laquiere I, Dehaen W, Parton RF, Vankelecom IFJ, Jacobs PA: A dimeric form of Jacobsen's catalyst for improved retention in a polydimethylsiloxane membrane. Tetrahedron: Asymmetry 1997, 8:3481-3487.
49. Papillon J, Schulz E, Gelinas S, Lessard J, Lemaire M: Towards the preparation of modified chiral electrodes for heterogeneous asymmetric catalysis: synthesis and electrochemical properties of (S,S)-5,5′-bis-[3-(3-methyl-pentyl)-thiophen-2-yl]-[2,2′]- bipyridine. Synth Met 1998, 96:155-160.
50. Breck DW: Zeolite Molecular Sieves. Malabar, FL: Krieger; 1984.
51. Davis ME: Zeolite-based catalysts for chemicals synthesis. Microporous Mesoporous Mater 1998, 21:173-182.
52. Arends IWCE, Sheldon RA, Wallau M, Schuchardt U: Oxidative transformations of organic compounds mediated by redox molecular sieves. Angew Chem Int Ed Engl 1997, 36:1145-1163.
53. Yaghi OM, Li HL, Davis C, Richardson D, Groy TL: Synthetic strategies, structure patterns, and emerging properties in the chemistry of modular porous solids. Account Chem Res 1998, 31:474-484. A review of the state-of-the-art in the 'modular' construction of solids with accessible porosity.
54. Davis ME, Lobo RF: Zeolite and molecular-sieve synthesis. Chem Mater 1992, 4:756-768.
55. 2O] assembled about a chiral metal complex. J Chem Soc Chem Commun 1995:425-426.
56. 2O. J Solid State Chem 1996, 125:228-233.
57. 16]. Chem Mater 1997, 9:2168-2173. One of some of the first examples [55,56,57-59] of imparting chirality into metallophosphate frameworks, in some cases by chiral transition metal complexes.
58. Gray MJ, Jasper JD, Wilkinson AP, Hanson JC: Synthesis and synchrotron microcrystal structure of an aluminophosphate with chiral layers containing tris(ethylenediamine)cobalt(III). Chem Mater 1997, 9:976-980. See annotation [57].
59. Peng PY, Bu XH, Tolbert SH, Stucky GD: Synthesis and characterizations of chiral tetrahedral cobalt phosphates with zeolite ABW and related frameworks. J Am Chem Soc 1997, 119:2497-2504. See annotation [57].
60. Gier T, Bu X, Feng P, Stucky GD: Synthesis and organization of zeolite-like materials with three-dimensional helical pores. Nature 1998, 395:154-157. A report on the synthesis of unique zeolite-type materials having two independent sets of three-dimensional crosslinked helical pores.
61. Corma A, Fuerte A, Iglesias M, Sanchez F: Preparation of new chiral dioxomolybdenum complexes heterogenized on modified USY-zeolites. Efficient catalysts for selective epoxidation of allylic alcohols. J Mol Catal A 1996, 107:225-234.
62. Corma A, Iglesias M, Mohino F, Sanchez F: Heterogenized catalysts on zeolites. Synthesis of new chiral Rh(I) complexes with (2S,4R)-trans-4-RCOO-2-(t-butylaminocarbonyl)pyrrolidines and (2S,4S)-cis-4-RCONH-2-(t-butylaminocarbonyl)pyrrolidines. Heterogenization on silica and a USY-zeolite and study of the role of support on their catalytic profile in hydrogenation of olefins. J Organomet Chem 1997, 544:147-156. Pyrrolidine-based chiral Rh-complexes were attached to the surface of mesoporous zeolite Y and silica via silane coupling groups; these systems were shown to catalyze asymmetric hydrogenation with high ees.
63. Carmona A, Corma A, Iglesias M, San Jose A, Sanchez F: Synthesis and characterization of new chiral Rh(I) complexes with N,N′-, and N,P-ligands. A study of anchoring on the modified zeolites and catalytic properties of heterogenized complexes. J Organomet Chem 1995, 492:11-21.
64. Carmona A, Corma A, Iglesias M, Sanchez F: Synthesis and characterization of chiral Cu(I) complexes with substituted-pyrrolidine-ligands bearing a triethoxysilyl group and preparation of heterogenized catalysts on USY-zeolites. Inorg Chim Acta 1996, 244:79-85.
65. Bein T: Inclusion chemistry of organometallics in zeolites. In Comprehensive Supramolecular Chemistry, vol 7. New York: Pergamon/Elsevier; 1996.
66. Ogunwumi SB, Bein T: Intrazeolite assembly of a chiral manganese salen epoxidation catalyst Chem Commun 1997:901-902. A chiral manganese salen complex was assembled from several components in the cages of the large-pore zeolite EMT. The catalyst showed a high ee in the epoxidation of styrene derivatives and was demonstrated to be truly heterogeneous.
67. Sabater MJ, Corma A, Domenech A, Fornes V, Garcia H: Chiral salen manganese complex encapsulated within zeolite Y: a heterogeneous enantioselective catalyst for the epoxidation of alkenes. Chem Commun 1997:1285-1286.
68. Kahlen W, Wagner HH, Hölderich WE: Zeolite effect in the enantioselective transhydrogenation over a Co-salen "ship-in-the-bottle" complex. Catal Lett 1998, 54:85-89.
69. Sabater MJ, Garcia S, Alvaro M, Garcia H, Scaiano JC: Intrazeolite photochemistry. 24. Enantioselective discrimination in the quenchng of chiral Mn(II)salen complexes encapsulated inside Y zeolite by chiral 2-butanols. J Am Chem Soc 1998, 120:8521-8522.
70. Leibovitch M, Olovsson G, Sundarababu G, Ramamurthy V, Scheffer JR, Trotter J: Asymmetric induction in photochemical reactions conducted in zeolites and in the crystalline state. J Am Chem Soc 1996, 118:1219-1220.
71. Sundarababu G, Leibovitch M, Corbin DR, Scheffer JR, Ramamurthy V: Zeolite as a host for chiral induction. Chem Commun 1996:2159-2160.
72. Joy A, Robbins RJ, Pitchumani K, Ramammurthy V: Asymmetrically modified zeolite as a medium for enantioselective photoreactions: reactions from spin forbidden excited states. Tetrahedron Lett 1997, 38:8825-8828. One of some contributions [70,71,72,73] on asymmetric induction in photochemical reactions in chemically modified zeolites.
73. Joy A, Scheffer JR, Corbin DR, Ramamurthy V: Enantioselective photoelectrocyclization within zeolites: tropolone methyl ether in chirally modified NaY. Chem Commun 1998:1379-1380. See annotation [72].
74. Kaprinidis NA, Landis MS, Turro NJ: Supramolecular control of photochemical enantiomeric induction and radical pair recombination in zeolites. Tetrahedron Lett 1997, 38:2609-2612.
75. Tas D, Jeanmart D, Parton RF, Jacobs PA: The immobilization of sulfonated Ru-BINAP chloride by anion exchange on layered double hydroxides. Stud Surf Sci Catal (Heterogeneous Catalysis and Fine Chemicals IV) 1997, 108:493-500.
76. Moller K, Bein T: Inclusion chemistry in periodic mesoporous hosts. Chem Mater 1998, 10:2950-2963.
77. Frunza L, Kosslick H, Landmesser H, Hoeft E, Fricke R: Host/guest interactions in nanoporous materials. I. The embedding of chiral salen manganese(III) complex into mesoporous silicates. J Mol Catal A 1997, 123:179-187.
78. O'Brien S, Tudor J, Maschmeyer T, O'Hare D: EXAFS analysis of a chiral alkene polymerization catalyst incorporated in the mesoporous silicate MCM-41. Chem Commun 1997:1905-1906.
79. 2]. Angew Chem Int Ed Engl 1998, 37:517-520.
80. Feast S et al.: Enantioselective dehydration of butan-2-ol using zeolite Y modified with dithiane oxides. J Catal 1997, 167:533-542. The authors demonstrate the kinetic resolution of enantiomers of butan-2-ol in an acid type Y zeolite modified with chiral dithiane oxides.
81. Willock DJ, Bethell D, Feast S, Hutchings GJ, King F, Page PCB: Creating chiral centers in zeolite Y by the introduction of R-1,3-dithiane 1-oxide as a modifier: computer simulation of the modifier stability. Topics Catal 1996, 3:77-89.
82. Feast S, Bethell D, Page PCB, King F, Rochester CH, Siddiqui MRH, Willock DJ, Hutchings GJ: Gas-phase catalytic asymmetric reaction using chirally modified microporous catalysts. J Chem Soc Chem Commun 1995:2409-2411.
83. Feast S, Bethell D, Bulman Page PC, King F, Rochester CH, Siddiqui MRH, Willock DJ, Hutchings GJ: Asymmetric resolution using modified zeolite catalysts. J Mol Catal A 1996, 107:291-295.
84. Langham C et al.: Catalytic heterogeneous aziridination of alkenes using microporous materials. Chem Commun 1998:1601-1602. The concept of chiral modification of zeolite cages was demonstrated in the enantioselective aziridination of olefins in the presence of acid Cu(II)HY zeolite containing chiral bis(oxazolines).
85. Morgenschweis K, Polkiehn E, Reschetilowski W: Controlling the enantioselective hydrogenation of ethyl pyruvate using zeolites as catalyst support. Stud Surf Sci Catal 1997, 108:167-174.
86. Boehmer U, Morgenschweis K, Reschetilowski W: Liquid phase asymmetric hydrogenation on Pt-containing zeolite Y catalysts. Catal Today 1995, 24:195-199.
87. Reschetilowski W, Boehmer U, Morgenschweis K: Asymmetric liquid phase hydrogenation of ethyl pyruvate over chirally modified platinum-containing ZSM-35 zeolite. Chem Ing Tech 1995, 67:205-207.
88. Van der Waal JC, Creyghton EJ, Kunkeler PJ, Tan K, van Bekkum H: Beta-type zeolites as selective and regenerable catalysts in the Meerwein-Ponndorf-Verley reduction of carbonyl compounds. Topics Catal 1997, 4:261-268.
89. Davis ME, Katz A, Ahmad WR: Rational design via imprinted nanostructured materials. Chem Mater 1996, 8:1820-1839.
90. Reetz MT, Jaeger K-E: Overexpression, immobilization and biotechnological application of Pseudomonas lipases. Chem Phys Lipids 1998, 93:3-14.
91. Adima A, Moreau JJE, Man MWC: Chiral organic-inorganic solids as enantioselective catalytic materials. J Mater Chem 1997, 7:2331-2333. A study of organic/inorganic hybrid materials obtained by co-condensation of functionalized chelate ligands and Rh-complexes with a silica precursor. The resulting porous solids are effective asymmetric catalysts for hydride transfer.
92. Pugin B: Immobilized catalysts for enantioselective hydrogenation: the effect of site isolation. J Mol Catal A 1996, 107:273-279.
93. Song CE, Yang JW, Ha H-J: Silica gel supported bis-cinchona alkaloid: a highly efficient chiral ligand for heterogeneous asymmetric dihydroxylation of olefins. Tetrahedron: Asymmetry 1997, 8:841-844. Grafting chemistry was used to heterogenize a functionalized alkaloid ligand on silica. This system conferred high enantioselectivity in the Os-catalyzed asymmetric dihydroxylation of olefins.
94. Wan KT, Davis ME: Design and synthesis of a heterogeneous asymmetric catalyst. Nature 1994, 370:449-450.
95. Wan KT, Davis ME: Asymmetric syntheses of naproxen by a new heterogeneous catalyst. J Catal 1995, 152:25-30.