Fluorous "racemic" mixture synthesis: Polysaccharide-based chiral columns for simultaneous demix and enantioseparation of racemic fluorous tagged compounds

Chirality

Volumn 20, Issue 3-4, 2008, Pages 597-603

  Tonoi, Takayuki ^a   Zhang, Wei ^b   Curran, Dennis P ^c   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Fluorous Technologies Inc   (United States)

^c UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Chiral HPLC column; Combinatorial chemistry; Enantioseparation; Fluorous racemic mixture synthesis (FRMS); Fluorous tag

Indexed keywords

FLUORINE; MANDELIC ACID DERIVATIVE; POLYSACCHARIDE;

ARTICLE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; RACEMIZATION; SEPARATION TECHNIQUE; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORINE; MAGNETIC RESONANCE SPECTROSCOPY; MANDELIC ACIDS; POLYSACCHARIDES; STEREOISOMERISM;

EID: 39749129747     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20487     Document Type: Article

References (68)

1. Morrison JD, Mosher HS, editors. Asymmetric organic reactions. Englewood Cliffs, NJ: Prentice-Hall; 1971.
2. Morrison JD, editor. Asymmetric synthesis, Vol. 1-5. New York: Academic Press; 1983.
3. Nicolaou KC, Hanko R, Hartwig W. Handbook of combinatorial chemistry: drugs, catalysts, materials. Weinheim: Wiley-VCH; 2002.
4. Shimizu KD, Snapper ML, Hoveyda AH. In: Jacobsen EN, Pfaltz A, Yamamoto H, editors. Comprehensive asymmetric catalysis, Vol. 3. Berlin: Springer; 1999. Ch. 39.
5. Wilson SR, Czarink AW, editors. Combinatorial chemistry: synthesis and application. New York: Wiley; 1997.
6. Miertus S, Fassina G. Combinatorial chemistry and technology. New York: Marcel Dekker; 1997.
7. Wilson SR, Czarnik AW. Combinatorial chemistry. New York: Wiley; 1997.
8. Reetz MT. Combinatorial and evolution-based methods in the creation of enantioselective catalysts. Angew Chem 2001;113:292-320.
9. Reetz MT. Combinatorial and evolution-based methods in the creation of enantioselective catalysts. Angew Chem Int Ed Engl 2001;40:284-310.
10. Bein T. Efficient assays for combinatorial methods for the discovery of catalysts. Angew Chem 1999;111:335-338.
11. Bein T. Efficient assays for combinatorial methods for the discovery of catalysts. Angew Chem Int Ed Engl 1999;38:323-326.
12. Hagemeyer A, Strasser P, Volpe AF Jr, editors. High-throughput screening in chemical catalysis. Weinheim: Wiley-VCH; 2004.
13. Devlin JP, editor. High-throughput screening. New York: Marcel Dekker; 1997.
14. Reetz MT. New methods for the high-throughput screening of enantioselective catalysts and biocatalysts. Angew Chem 2002;114:1391-1394.
15. Reetz MT. New methods for the high-throughput screening of enantioselective catalysts and biocatalysts. Angew Chem Int Ed Engl 2002;41:1335-1338.
16. Jandeleit B, Schaefer DJ, Powers TS, Turner HW, Weinberg WH. Combinatorial material science and catalysis. Angew Chem 1999;111:2648-2689.
17. Jandeleit B, Schaefer DJ, Powers TS, Turner HW, Weinberg WH. Combinatorial material science and catalysis. Angew Chem Int Ed Engl 1999;38:2494-2532.
18. Finn MG. Emerging methods for the rapid determination of enantiomeric excess. Chirality 2002;14:534-540.
19. Kagan HB. New screening methodologies or combinatorial chemistry applied to asymmetric catalysts. J Organomet Chem 1998;567:3-6.
20. Shimizu KD, Snapper ML, Hoveyda AH. High-throughput strategies for the discovery of catalysts. Chem Eur J 1998;4:1885-1889.
21. 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 1996;108:1776-1779.
22. 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.
23. 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.
24. Francis MB, Jacobsen EN. Discovery of novel catalysts for alkene epoxidation from metal-binding combinatorial libraries. Angew Chem 1999;111:987-991.
25. Francis MB, Jacobsen EN. Discovery of novel catalysts for alkene epoxidation from metal-binding combinatorial libraries. Angew Chem Int Ed Engl 1999;38:937-941.
26. Reetz MT. Super-high-throughput screening of enantioselective catalysts by using capillary array electrophoresis. Angew Chem 2000;112:4049-4052.
27. Reetz MT. Super-high-throughput screening of enantioselective catalysts by using capillary array electrophoresis. Angew Chem Int Ed Engl 2000;39:3891-3893.
28. Markert C, Pfaltz A. Screening of chiral catalysts and catalyst mixtures by mass spectrometric monitoring of catalytic intermediates. Angew Chem 2004;116:2552-2554.
29. Markert C, Pfaltz A. Screening of chiral catalysts and catalyst mixtures by mass spectrometric monitoring of catalytic intermediates. Angew Chem Int Ed Engl 2004;43:2498-2500.
30. Reetz MT, Tielmann P, Eipper A, Ross A, Schlotterbeck G. A high-throughput NMR-based ee-assay using chemical shift imaging. Chem Commun 2004;1366-1367.
31. Gladysz J, Curran DP, Horvath IT, editors. Handbook of fluorous chemistry. Weinheim: Wiley-VCH; 2004.
32. Mikami K, editor. Green reaction media in organic synthesis. Oxford: Blackwell; 2005.
33. Zhang W. Fluorous technologies for solution-phase high-throughput organic synthesis. Tetrahedron 2003;59:4475-4489.
34. Curran DP. Strategy-level separations in organic synthesis: from planning to practice. Angew Chem Int Ed Engl 1998;37:1174-1196.
35. Matsuzawa H, Mikami K. Highly efficient discrimination of fluorous tags by β-cyclodextrin columns: new isolation method for fluorous mixture synthesis. Synlett 2002;1607-1612.
36. Nakamura Y, Takeuchi S, Okumura K, Ohgo Y, Matsuzawa H, Mikami K. Enantiomeric resolution of fluorous mixture by chiral CD columns: asymmetric reduction of a mixture of fluorous ketones. Tetrahedron Lett 2003;44:6221-6225.
37. Matsuzawa H, Mikami K. Efficient enantiomeric resolution via introduction of a fluorous tag as a resolving reagent with β-cyclodextrin columns: model study on fluorinated O-acetylmandelate and ibuprofen amide. Tetrahedron Lett 2003;44:6227-6230.
38. Curran DP, Dandapani S, Werner S, Matsugi M. Fluorous columns are superior to cyclodextrin columns for demixing in fluorous mixture synthesis: when and why to use fluorous silica gel. Synlett 2004;1545-1548.
39. Mikami K, Matsuzawa H, Takeuchi S, Nakamura U, Curran DP. β-Cyclodextrin columns for separation of fluorous and non-fluorous compounds: how to use β-cyclodextrin columns in fluorous mixture synthesis and racemic synthesis. Synlett 2004;2713-2716.
40. Catalog of SUMICHIRAL OA-7000 series. Available at: http://www.scas.co. jp/.
41. Pirkle WH, Pochapsky TC. Considerations of chiral recognition relevant to the liquid chromatography separation of enantiomers. Chem Rev 1989;89:347-362.
42. Okamoto Y, Yashima E. Polysaccharide derivatives for chromatographic separation of enantiomers. Angew Chem 1998;110:1072-1095.
43. Okamoto Y, Yashima E. Polysaccharide derivatives for chromatographic separation of enantiomers. Angew Chem Int Ed Engl 1998;37:1020-1043.
44. Yashima E, Yamamoto C, Okamoto Y. NMR studies of chiral discrimination relevant to the liquid chromatographic enantioseparation by a cellulose phenylcarbamate derivative. J Am Chem Soc 1996;118:4036-4048.
45. Yamamoto C, Okamoto Y. Optically active polymers for chiral separation. Bull Chem Soc Jpn 2004;77:227-257.
46. Kubota T, Yamamoto C, Okamoto Y. Phenylcarbamate derivatives of cellulose and amylose immobilized onto sillica gel as chiral stationary phases for high-performance liquid chromatography. J Polym Sci Part A: Polym Chem 2004;42:4704-4710.
47. Catalog of CHIRALCEL® and CHIRALPAK® series. Available at: http://www.daicelchiral.com.
48. Winstead MB, Dougherty DA. Relationship of molecular structure to in vivo scintigraphic distribution of carbon-11-labeled compounds. 4. Carbon-11-labeled mandelonitriles, mandelic acids and their esters. J Med Chem 1978;21:215-217.
49. Linhart I, Gut I, Smejkal J, Novak J. Biotransformation of styrene in mice: stereochemical aspects. Chem Res Toxicol 2000;13:36-44.
50. Ishii A, Kojima J, Mikami K. Asymmetric catalytic Friedel-Crafts reaction of silyl enol ethers with fluoral: a possible mechanism of the Mukaiyama-aldol reactions. Org Lett 1999;1:2013-2016.
51. Ishii A, Mikami K. Asymmetric Friedel-Crafts reactions of vinyl ethers with fluoral catalyzed by chiral binaphthol-derived titanium catalysts. J Fluorine Chem 1999;97:51-55.
52. Ishii A, Soloshonok VA, Mikami K. Asymmetric catalysis of the Friedel-Crafts Reaction with Fluoral by chiral binaphthol-derived titanium catalysts through asymmetric activation. J Org Chem 2000;65:1597-1599.
53. Gathergood N, Zhuang W, Jorgensen KA. Catalytic enantioselective Friedel-Crafts reactions of aromatic compounds with glyoxylate: a simple procedure for the synthesis of optically active aromatic mandelic acid esters. J Am Chem Soc 2000;122:12517-12522.
54. Zhuang W, Gathergood N, Hazell RG, Jorgensen KA. Catalytic, highly enantioselective Friedel-Crafts reactions of aromatic and heteroaromatic compounds to trifluoropyruvate: a simple approach for the formation of optically active aromatic and heteroaromatic hydroxy trifluoromethyl esters. J Org Chem 2001;66:1009-1013.
55. Yuan Y, Wang X, Li X, Ding K. Highly enantioselective Friedel-Crafts reaction of aromatic amines with ethyl glyoxylate catalyzed by chiral titanium (TV) complexes: practical synthesis of aminomandelic acid derivatives. J Org Chem 2004;69:146-149.
56. Mikami K, Angelaud R, Ding K, Ishii A, Tanaka A, Sawada N, Kudo K, Senda M. Asymmetric activation of chiral alkoxyzinc catalysts by chiral nitrogen activators for dialkylzinc addition to aldehydes: super high-throughput screening of combinatorial libraries of chiral ligands and activators by HPLC-CD/UV and HPLC-OR/RIU systems. Chem Eur J 2001;7:730-737.
57. Angelaud R, Matsumoto Y, Korenaga T, Kudo K, Senda M, Mikami K. Optical rotation per refractive index unit, or enantiomeric (e) factor, for screening enantioselective catalysts through asymmetric activation or carbohydrates. Chirality 2000;12:544-547.
58. Ding K, Ishii A, Mikami K. Super high throughput screening (SHTS) of chiral ligands and activators: asymmetric activation of chiral diol-zinc catalysts by chiral nitrogen activators for the enantioselective addition of diethylzinc to aldehydes. Angew Chem 1999;111:519-523.
59. Ding K, Ishii A, Mikami K. Super high throughput screening (SHTS) of chiral ligands and activators: asymmetric activation of chiral diol-zinc catalysts by chiral nitrogen activators for the enantioselective addition of diethylzinc to aldehydes. Angew Chem Int Ed Engl 1999;38:497-501.
60. Reetz MT, Kuhling KM, Hinrichs H, Deege A. Circular dichroism as a detection method in the screening of enantioselective catalysts. Chirality 2000;12:479-482.
61. Xu L, Shen X, Zhang C, Mikami K. Chiral aminonaphthol-catalyzed enantioselective carbonyl addition of diethylzinc to aromatic aldehydes high-throughput screened by CD-HPLC analysis. Chirality 2005;17:476-480.
62. Luo ZY, Zhang QS, Oderaotoshi Y, Curran DP. Fluorous mixture synthesis: a fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds. Science 2001;291:1766-1769.
63. Zhang W, Luo Z, Chen CH-T, Curran DP. Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis. J Am Chem Soc 2002;124:10443-10450.
64. Zhang QS, Rivkin A, Curran DP. Quasiracemic synthesis: concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine. J Am Chem Soc 2002;124:5774-5781.
65. Nakanishi K, Berova N, Woody RW, editors. Circular dichroism. Principles and application. Weinheim: VCH; 1994. p 541.
66. Bertucci C, Salvadori P, Guimaraes LFL. Determination of optical purity by high-performance liquid chromatography upon non-chiral stationary phases with dual circular dichroism/absorption detection. J Chromatogr 1994;666:535-539.
67. Salvadori P, Bertucci C, Rosini C. Circular dichroism detection in HPLC. Chirality 1991;3:376-385.
68. Mannschreck A. Chiroptical detection during liquid chromatography: applications to stereoanalysis and stereodynamics. Chirality 1992;4:163-169.