Chiral catalysis on solids

Current Opinion in Solid State and Materials Science

Volumn 3, Issue 1, 1998, Pages 86-93

  Baiker, Alfons ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

TA tartaric acid

Indexed keywords

EID: 0001961862     PISSN: 13590286     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-0286(98)80070-3     Document Type: Article

References (56)

1. Sheldon RA. Chirotechnology. 1993;Marcel Deckker Inc, New York.
2. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;John Wiley & Sons Inc, New York.
3. Baiker A, Blaser HU. Enantioselective catalysis and reactions. Ertl G, Knoezinger H, Weitkamp J. Handbook of Heterogeneous Catalysis. 5:1997;2422-2436 VCH, Weinheim, General review on heterogeneous enantioselective catalysis.
4. Davis ME. Catalytic materials via molecular imprinting. CaTTech. 1:1997;19-26 State-of-the-art of imprinting is discussed.
5. McFadden CF, Cremer PS, Gellman AJ. Adsorption of chiral alcohols on chiral metal surfaces. Langmuir. 12:1996;2483-2487 First report of a chiral metal surface.
6. Sieger A. The flow stress of high-purity refractory body-centered cubic metals and its modification by atomic defects. J Phys IV. 5:1995;45-65.
7. Tai A, Harada T. Asymmetrically modified nickel catalysts. Iwasawa Y. Tailored Metal Catalysts. 1986;265-324 Riedel Publishing Co, Dordrecht.
8. Webb G, Wells PB. Asymmetric hydrogenation. Catal Today. 12:1992;319-337.
9. Sugimura T, Osawa T, Nakagawa S, Harada T, Tai A. Stereochimical studies of the enantio-differentiating hydrogenation of various prochiral ketones over tartaric acid-modified nickel catalyst. Studies Surf Sci Catal. 101:1996;231-240.
10. Osawa T, Harada T, Tai A. Enantio-differentiating hydrogenation of prochiral ketones over modified nickel. Catal Today. 37:1997;465-480 Summarizes the knowledge on the control of enantioselectivity in hydrogeneration of ketones over nickel modified by tartaric acid.
11. Osawa T, Harada T, Tai A, Takayasu O, Matsuura I. Enantio-differentiating hydrogenation of 3-alkanones with asymmetrically modified fine nickel powder. Blaser HU, Baiker A, Prins R. Heterogeneous Catalysis and Fine Chemicals IV. 1997;199-206 Elsevier Science, Amsterdam.
12. Keane MA. Interaction of optically active tartaric acid with a nickel silica catalyst: role of both the modification and reaction media in determining enantionselectivity. Langmuir. 13:1997;41-50.
13. Blaser HU, Jalett HP, Müller M, Studer M. Enantioselective hydrogenation of α-ketoesters using cinchona modified platinum catalysts and related systems: a review. Catal Today. 37:1997;441-463.
14. Baiker A. Progress in asymmetric heterogeneous catalysis: Design of novel chirally modified platinum metal catalysts. J Mol Catal A. 115:1997;473-493 The state-of-the-art in designing novel chirally modified platinum catalysis is discussed.
15. Minder B, Mallat T, Baiker A, Wang G, Heinz T, Pfaltz A. A novel aminoalcohol modified for the enantioselective hydrogenation of ethyl pyruvate on platinum/alumina. J Catal. 154:1995;371-378.
16. Schürch M, Mallat T, Baiker A, Heinz T, Pfaltz A. Design of new modifiers for the enantioselective hydrogenation of ethyl pyruvate. J Catal. 1998;. in press.
17. Minder B, Schürch M, Mallat T, Baiker A, Heinz T, Pfaltz A. Enantioselective hydrogenation of ethyl pyruvate over Pt/alumina modified by (R)-1-(1-naphthyl)ethylamine derivatives. J Catal. 160:1996;261-268.
18. Schürch M, Schwalm O, Mallat T, Weber J, Baiker A. Enantioselective hydrogenation of ketopantolactone. J Catal. 169:1997;275-286.
19. Mallat T, Bodmer M, Baiker A. Enantioselective hydrogenation of trifluoroacetophenone. Catal Lett. 44:1997;95-99.
20. Bodmer M, Mallat T, Baiker A. Enantioselective hydrogenation of trifluoroacetophenone over platinum/alumina modified by cinchonidine. Herkes FE. Catalysis in Organic Reactions. 1998;Marcel Dekker, New York. in press.
21. 3 modified by cinchona alkaloids. Tetrahedron Asymmetry. 8:1997;2133-2140.
22. Nitta Y, Kobiro K. Conversion dependence of enantioselective hydrogenation of E-α-phenylcinnamic acid on cinchonidine-modified Pd/titania catalyst. Chem Lett. 1996;897-898.
23. Borszeky K, Mallat T, Baiker A. Enantioselective hydrogenation of 2-methyl-2-pentenoic acid over cinchonidine-modified Pd/alumina. Catal Lett. 41:1996;199-202.
24. Borszeky K, Mallat T, Aeschiman R, Schweizer WB, Baiker A. Enantioselective hydrogenation of pyruvic acid oxime to alanine on Pd/alumina. J Catal. 161:1996;451-458.
25. GV Smith, Cheng JJ, Song RZ. New enantioselective heterogeneous catalysts. Catal Lett. 45:1997;73-78.
26. Feast S, Rafiq M, Siddiqui H, Wells RPK, Willock DJ, King F, Rochester CH, Bethell D, Bulman Page PC, Hutchings GJ. Enantioselective dehydration of butan-2-ol using zeolite-Y modified with dithiane oxides. J Catal. 167:1997;533-542 First example of a gas phase enantioselective reaction heterogeneously catalyzed by a zeolite.
27. Feast S, Bethell D, Bulman Page PC, King F, Rochester CH, Siddiqui H, Willock DJ, Hutchings GJ. Enantioselection using modified zeolite catalysts. J Mol Catal A. 107:1996;291-295.
28. Aglietto M, Chiellini E, Dantone S, Ruggeri G, Solaro R. Chiral polymer catalysts in preparative organic chemistry: a critical overview. Pure Appl Chem. 60:1988;415-430.
29. Itsuno S, Sakakura M, Ito K. Polymer-supported poly(amino acids) as new asymmetric epoxidation catalyst of α,β-unsaturated ketones. J Org Chem. 55:1990;6047-6049.
30. Flisak JR, Gombatz KJ, Holmes MM, Jarmas AA, Lantos I, Mendelson WL, Novack VJ, Remich JJ, Snyder L. A practical, enantioselective syntheses of SK&F 104353. J Org Chem. 58:1993;6247-6254.
31. Lasterra-Sànchez ME, Felfer U, Mayon P, Roberts SM, Thornton SR, Todd CJ. Development of the Julià asymmetric epoxidation reaction. Part 1. Application of the oxidation to enones other than chalcones. J Chem Soc Perkin Trans 1. 1996;343-348 Broadening of the range of reactants epoxidized with polypeptide catalysts.
32. Kroutil W, Lasterra-Sànchez ME, Maddell SJ, Mayon P, Morgan P, Roberts SM, Thornton SR, Todd CJ, Tüter M. Development of the Julià asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters. J Chem Soc Perkin Trans 1. 1996;2837-2844.
33. Bentley PA, Bergeron S, Cappi WM, Hibbs DE, Hursthouse MB, Nugent TC, Pulido R, Roberts SM, Wu LE. Asymmetric epoxidation of enones employing polymeric α-amino acids in non-aqueous media. J Chem Soc Chem Commun. 1997;739-740.
34. Kim HJ, Jackson WR. Substituent effects on the enantioselective hydrocyanation of aryl aldehydes. Tetrahedron Asymmetry. 5:1994;1541-1548.
35. Tanaka K, Mori A, Inoue S. The cyclic dipeptide cyclo[(S)-phenylalanyl-(S)-histidyl] as a catalyst for asymmetric addition of hydrogen cyanide to aldehydes. J Org Chem. 55:1990;181-185.
36. Danda H. Essential factors in asymmetric hydrocyanation catalyzed by cyclo(-(R)-Phe-(R)-His-). Synlett. 1991;263-264.
37. Shvo Y, Gal M, Becker Y, Elgavi A. Asymmetric hydrocyanation of aldehydes with cyclo dipeptides: a new mechanistic approach. Tetrahedron Asymmetry. 7:1996;911-924.
38. 2Zn addition mediated by a polymer-incorporated titanate. Helv Chim Acta. 80:1997;2027-2032 Application of dendritic molecules as cross-linkers in polymer-based enantioselective catalysts.
39. Blaser HU, Fugin B. Scope and limitations of the application of heterogeneous enantioselective catalyst. Jannes G, Dubois V. Chiral Reactions in Heterogeneous Catalysis. 1995;33-57 Pleum Press, New York, Important aspects of immobilized enantioselective hydrogeantion catalysts.
40. Wan KT, Davis ME. Asymmetric syntheses of naproxen by a new heterogeneous catalysts. J Catal. 152:1995;25-30.
41. Hau H, Janda KD. Soluble polymer-bound ligand-accelerated catalysis: asymmetric dihydroxylation. J Am Chem Soc. 118:1996;7632-7633 Method of catalyst recovery based on the use of chiral catalysts or auxillaries supported on a soluble polymer is demonstrated.
42. Vankelekom IFJ, Tas D, Parton RF, van de Vyver V, Jacobs PA. Chiral catalytic membranes. Int Ed Engl Angew Chem. 35:1996;1346-1348 Immobilization of a chiral catalyst in an elastomeric membrane.
43. Flach HN, Grassert I, Oehme G, Capka M. New insoluble surfactant systems as aids in catalysis. A convenient method for nonbonded immobilisation of catalytically active transition metal complexes. Colloid Polym Sci. 274:1996;261-268 Catalysts remain homogeneous.
44. 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. 107:1996;225-234.
45. Minutolo F, Pini D, Petri A, Salvadori P. Heterogeneous asymmetric epoxidation of unfunctionalized olefins catalyzed by polymer-bound (salen)manganese complexes. Tetrahedron Asymmetry. 7:1996;2293-2302.
46. Minutolo F, Pini D, Petri A, Salvadori P. Polymer-bound chiral (salen)Mn(III) complexes as a heterogeneous catalyst in rapid and clean enantioselective epoxidation of unfunctionalized olefins. Tetrahedron Lett. 37:1996;3375-3378.
47. Sabater MJ, Corma A, Domenech A, Fornés V, Garcia H. Chiral salen manganese complex encapsulated within zeolite Y: a heterogeneous enantioselective catalyst for the epoxidation of alkenes. J Chem Soc Chem Commmun. 1997;1285-1286.
48. Ogunwumi SB, Bein T. Intrazeolite assembly of a chiral manganese salen epoxidation catalyst. J Chem Soc Chem Commun. 1997;901-902.
49. Frunza L, Kosslick H, Landmesser H, Höft 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. 123:1997;179-187.
50. Song CE, Yang JW, Ha HJ. Silica gel supported bis-cinchona alkaloid: a highly efficient chiral ligand for heterogeneous asymmetric dihydroxylation of olefins. Tetrahedron Asymmetry. 8:1997;841-844.
51. Nandanan E, Sudalai A, Ravindranathan T. New polymer supported cinchona alkaloids for heterogeneous catalytic asymmetric dihydroxylation of olefins. Tetrahedron Lett. 38:1997;2577-2580.
52. Song CE, Yang JW, Ha HJ, Lee S. Efficient and practical polymeric catalysts for heterogeneous dihydroxylation of olefins. 7:1996;645-648.
53. Shimazu S, Ro K, Sento T, Ichikuni N, Uematsu T. Asymmetric hydrogenation of α,β-unsaturated carboxylic acid esters by rhodium(I)-phosphine complexes supported on smectites. J Mol Catal A. 107:1996;297-303.
54. Pugin B. Immobilized catalysts for enantioselective hydrogenation: The effect of site-isolation. J Mol Catal A. 107:1996;273-279.
55. Irurre J, Serrat AF, Rosanas F. Polymer-supported chiral diol as ligand of Ti(IV) of enantioselective Diels - Alder reaction. Chirality. 9:1997;191-197.
56. Canali L, Karjalainen JK, Sherrington DC, Hormi O. Efficient polymer-supported sharpless alkene epoxidation catalyst. J Chem Soc Chem Commun. 1997;123-124.