Optical rotation per refractive index unit, or enantiomeric (e) factor, for screening enantioselective catalysts through asymmetric activation or carbohydrates

Chirality

Volumn 12, Issue 5-6, 2000, Pages 544-547

  Angelaud, Remy ^a   Matsumoto, Yousuke ^a   Korenaga, Toshinobu ^a   Kudo, Kenichi ^b   Senda, Masaaki ^b   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Hachioji shi   (Japan)

Author keywords

Asymmetric activation; Combinatorial catalysts; Enantiomeric (e) factor; High throughput screening; Optical rotation; Refractive index

Indexed keywords

ALDEHYDE; DIETHYLZINC;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; REFRACTION INDEX; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034034632     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<544::aid-chir43>3.0.co;2-a     Document Type: Article

References (39)

1. a) Jacobsen EN, Pfaltz A, Yamamoto H. Comprehensive asymmetric catalysis, vol. I-III. Berlin: Springer; 1999.
2. b) Gawley RE, Aube J. Principles of asymmetric synthesis. London: Pergamon; 1996.
3. c) Doyle MP. Advances in catalytic processes, Vol. I-II. London: JAI Press; 1995, 1998.
4. d) Noyori R. Asymmetric catalysis in organic synthesis. New York: Wiley; 1994.
5. e) Brunner H, Zettlmeier W. Handbook of enantioselective catalysis. Weinheim: VCH; 1993.
6. f) Ojima I. Catalytic asymmetric synthesis. New York: VCH; 1993 and 2000.
7. g) Kagan HB. Comprehensive organic chemistry, vol. 8. Oxford: Pergamon; 1992.
8. h) Bosnich B. Asymmetric catalysis. Dordrecht: Martinus Nijhoff; 1986.
9. a) Mikami K, Matsukawa S. Asymmetric synthesis by enantiomer-selective activation of racemic catalysts. Nature 1997;385:613-615.
10. b) Volk T, Korenaga T, Matsukawa S, Terada M, Mikami K. Asymmetric activation of chiral BINOL-zirconium catalysts: effect of a product-like activator. Chirality 1998;10:717-721.
11. c) Matsukawa S, Mikami K. Chiral drugging: chiral activator-induced enantiomer selective activation of racemic catalyst for asymmetric amplifying catalysis. Enantiomer 1996; 1:69-73.
12. d) Ohkuma T, Doucet H, Pham T, Mikami K, Korenaga T, Terada M, Noyori R. Asymmetric activation of racemic ruthenium(II) complexes for enantioselective hydrogenation. J Am Chem Soc 1998; 120:1086-1087.
13. e) Mikami K, Korenaga T, Terada M, Ohkuma T, Pham T, Noyori R. Conformationally flexible biphenylphosphane ligands for Ru-catalyzed enantioselective hydrogenation. Angew Chem Int Ed Engl 1999;38:495-497.
14. a) Special issue on combinatorial library. No. 3. Acc Chem Res 29:1996.
15. b) Reviews: Jandeleit B, Schaefer DJ, Powers TS, Turner HW, Weinberg WH. Combinatorial materials science and catalysis. Angew Chem Int Ed Engl 1999;38:2494-2532.
16. c) Balkenhohl F, von dem Bussche-Hunnefeld C, Lansky A, Zechel C. Combinatorial synthesis of small organic molecules. Angew Chem Int Ed Engl 1996;35:2288-2337.
17. d) Gennari C, Nestler HP, Piarulli U, Salom B. Combinatorial libraries: studies in molecular recognition and the quest for new catalysts. Liebigs Ann 1997;637.
18. e) Wilson SR, Czarink AW. Combinatorial chemistry: synthesis and application. New York: Wiley; 1997.
19. f) Miertus S, Fassina G. Combinatorial chemistry and technology. New York: Marcel Dekker; 1997.
20. Devlin JP. High throughput screening. New York: Marcel Dekker; 1997.
21. a) Burgess K, Lim H-J, Porte AM. Sulikowski GA. New catalysts and conditions for a C-H insertion reaction identified by high throughput catalyst screening. Angew Chem Int Ed Eng 1996;35:220-222.
22. b) Porte AM, Reibenspies J, Burgess K. Design and optimization of new phosphine oxazoline ligands via high-throughput catalyst screening. J Am Chem Soc 1998;120:9180-9187.
23. c) 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 Eng 1996;35:1668-1671.
24. d) 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 Eng 1997;36:1703-1707.
25. e) Krueger CA, Kuntz KW, Dzierba CD, Wirschun WG, Gleason JD, Snapper ML, Hoveyda AH. Ti-catalyzed enantioselective addition of cyanide to imines. A practical synthesis of optically pure α-amino acids. J Am Chem Soc 1999;121: 4284-4285.
26. f) 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.
27. g) Francis MB, Jacobsen EN. Discovery of novel catalysts for alkene epoxidation from metal-binding combinatorial libraries. Angew Chem Int Ed Eng 1999;38:937.
28. h) Liu GA, Ellman J. A general solid-phase synthesis strategy for the preparation of 2-pyrrolidinemethanol ligands. J Org Chem 1995;60:7712-7713.
29. a) Reetz MT, Zonta A, Schimossek K, Liebeton K, Jaeger K-E. Creation of enantioselective biocatalysts for organic chemistry by in vitro evolution. Angew Chem Int Ed Eng 1997;36:2830-2832.
30. b) Klein G, Reymond J-L. Enantioselective fluorogenic assay of acetate hydrolysis for detecting lipase catalytic antibodies. Helv Chim Acta 1999;82:400-406.
31. In homogeneous catalysis: Reetz MT, Becker MH, Kuhling KM, Holzwarth A. Time-resolved IR-thermographic detection and screening of enantioselectivity in catalytic reactions. Angew Chem Int Ed Eng 1998; 37:2647-2650.
32. a) Guo J, Wu J, Siuzdak G, Finn MG. Measurement of enantiomeric excess by kinetic resolution and mass spectrometry. Angew Chem Int Ed Eng 1999;38:1755-1758.
33. b) Reetz MT, Becker MH, Klein H-W, Steckigt DA. A method for high-throughput screening of enantioselective catalysts. Angew Chem Int Ed Eng 1999;38:1758-1761.
34. Ding K, Ishii A, Mikami K. Super high throughput screening (SHTS) of chiral ligands and activators: asymmetric activation of chiral diolzinc catalysts by chiral nitrogen activators for the enantioselective addition of diethylzinc to aldehydes. Angew Chem Int Ed Eng 1999;38: 497-501.
35. a) Kuhn W. The physical significance of optical rotatory power. Trans Faraday Soc 1930;26:293-308.
36. b) Lowry TM, French HS. The rotatory dispersive power of organic compounds. Part XX. Rotatory dispersion and circular dichroism of camphor-β-sulphonic acid in the region of absorption. J Chem Soc 1932;2654-2656.
37. Drake AF, Gould JM, Mason SF. Simultaneous monitoring of light-absorption and optical activity in the liquid chromatography of chiral substances. J Chromatogr 1980;202:239-245.
38. a) Salvadori P, Bertucci C, Rosini C. Circular dichroism detection in HPLC. Chirality 1991;3:376-385.
39. b) Salvadori P, Bertucci C, Rosini C. In: Nakanishi K, Berova N, Woody RW, editors. Circular dichroism. Principles and application. Weinheim: VCH; 1994. p 541-560.