Enantiomers of (2R*,3R*)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrolidine-3-carboxylic acid as novel chiral resolving agents

Tetrahedron Asymmetry

Volumn 19, Issue 3, 2008, Pages 309-317

  Piwowarczyk, Katarzyna ^a   Zawadzka, Anna ^a   Roszkowski, Piotr ^a   Szawkało, Joanna ^a   Leniewski, Andrzej ^a   Maurin, Jan K ^b,c   Kranz, Darius ^a   Czarnocki, Zbigniew ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b NATIONAL MEDICINES INSTITUTE   (Poland)

^c INSTITUTE OF ATOMIC ENERGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2,3,4 TRICHLOROPHENYL)ETHYL 1 METHYL 5 OXO 2 PHENYLTETRAHYDRO 1H PYRROLIDINE 3 CARBOXYLATE; 1 (3,4 DIMETHOXYPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 1 (3,4 DIMETOXYBENZYL) 6,7 DIMETOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 1 METHYL 5 OXO 2 PHENYL N [1 PHENYLETHYL]TETRAHYDRO 1H PYRROLIDINE 3 CARBOXOAMIDE; 1 METHYL 5 OXO 2 PHENYLTETRAHYDRO 1H PYRROLIDINE 3 CARBOXYLIC ACID; 2 (1,3 BENZODIOXOL 5 YL) 1 METHYL 5 OXOTETRAHYDRO 1H PYRROLIDINE 3 CARBOXYLIC ACID; 2 (2 CHLOROPHENYL) 1 METHYL 5 OXOTETRAHYDRO 1H PYRROLIDINE 3 CARBOXYLIC ACID; 2 (4 METHOXYPHENYL) 1 METHYL 5 OXOTETRAHYDRO 1H PYRROLIDINE 3 CARBOXYLIC ACID; 2 OXO 1,2 DIPHENYLETHYL 1 METHYL 5 OXO 2 PHENYLTETRAHYDRO 1H PYRROLIDINE 3 CARBOXYLATE; 6,7 DIMETHOXY 1 (2 PHENYLETHYL) 1,2,3,4 TETRAHYDROISOQUINOLINE; CARBOXYLIC ACID DERIVATIVE; SALSOLIDINE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COLUMN CHROMATOGRAPHY; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 39149112764     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.01.014     Document Type: Article

References (46)

1. Murray R.K., Granner D.K., Mayes P.A., and Rodwell V.W. Harper's Biochemistry (1999), McGraw-Hill Medical, New York
2. Eliel E.L., and Wilen S.H. Stereochemistry of Organic Compounds (1994), John Wiley & Sons, New York
3. Yamamoto H., and Futatsugi K. Angew. Chem., Int. Ed. 44 (2005) 1924-1942
4. Finn M.G., and Sharpless K.B. J. Am. Chem. Soc. 113 (1991) 113
5. Juntilla M.H., and Hormi O.E.O. J. Org. Chem. 69 (2004) 4816-4820
6. Mijs W.J., and deJonge C.R.H.I. Organic Syntheses by Oxidation with Metal Compounds (1986), Plenum Press, New York pp 642-645
7. Charette A.B., Prescott S., and Brochu C.J. J. Org. Chem. 60 (1995) 1081-1083
8. Behr J.P., Girodeau J.M., Hayward R.C., Lehn J.M., and Sauvage J.P. Helv. Chim. Acta 63 (1980) 2096-2111
9. Behr J.P., Burrows C.J., Heng R., and Lehn J.M. Tetrahedron Lett. 26 (1985) 215-218
10. Hollmann G., and Vogtle F. Chem. Ber. 117 (1984) 1355-1363
11. Seebach D., Beck A.K., and Heckel A. Angew. Chem., Int. Ed. 40 (2001) 92-138
12. Datta S., and Roesky P.W. Z. Anorg. Allg. Chem. 632 (2006) 972-974
13. Speckamp W.N. Pure Appl. Chem. 68 (1996) 695-698
14. De Koning H., Hiemstra H., Moolenaar M.J., and Speckamp W.N. Eur. J. Org. Chem. (1998) 1729-1737
15. Gawroński J., and Gawrońska K. Tartaric and Malic Acids in Synthesis (1999), John Wiley & Sons, New York
16. Vries T., Wynberg H., van Echten E., Koek J., ten Hoeve W., Kellogg R.M., Broxterman Q.B., Minnaard A., Kaptein B., van der Sluis S., Hulshof L., and Kooistra J. Angew. Chem., Int. Ed. 37 (1998) 2349-2354
17. Jacques J., Collet A., and Wilen S.H. Enantiomers, Racemates, and Resolutions (1981), John Wiley & Sons, New York
18. Pirkle W.H., and House D.W. J. Org. Chem. 44 (1979) 1957-1960
19. Ahn S., Ramirez J., Grigorean G., and Lebrilla C.B. J. Am. Soc. Mass Spectrom. 12 (2001) 278-287
20. Ku{combining double acute accent}hnle A., Linderoth T.R., Hammer B., and Besenbacher F. Nature (London) 415 (2002) 891-893
21. Castagnoli N. J. Org. Chem. 34 (1969) 3187-3189
22. Bose A.K., Manhas M.S., Ghosh M., Raju V.S., Tabei T., and Urbańczyk-Lipkowska Z. Heterocycles 30 (1990) 741-744
23. Maurin J.K., Czarnocki Z., Wojtasiewicz K., Maleszewska E., Magdziak K., and Paluchowska B. J. Mol. Struct. 610 (2002) 33-40
24. Zwicker B.M.G., and Robinson R.J. J. Am. Chem. Soc. 64 (1942) 790-793
25. Gould R.O., and Walkinshaw M.D. J. Am. Chem. Soc. 106 (1984) 7840-7842
26. Bialonska A., and Ciunik Z. Crystengcomm 6 (2004) 276-279
27. Maurin J.K., Lis T., Zawadzka A., and Czarnocki Z. Acta Crystallogr., Sect. E 62 (2006) o694-o696
28. Selwe C., and Seyer R. Tetrahedron Lett. (1975) 1219
29. Gluchov N.A., Koton M.M., and Koroleva Z.A. Zh. Obshch. Khim. 28 (1958) 3277-3282
30. Umino N., Iwakuma T., and Itoh I. Chem. Pharm. Bull. 27 (1979) 1479-1481
31. Yamada K., Takeda M., and Iwakuma T. J. Chem. Soc., Perkin Trans. 1 (1983) 265-270
32. Hajipour A.R., and Hantehzadeh M. J. Org. Chem. 64 (1999) 8475-8478
33. Sheldrick, G. M. shelxs 97. Program for Solving Crystal Structures. University of Goettingen, 1997, Germany.
34. Sheldrick, G. M. shelxl 97. Program for Crystal Structure Refinement. University of Goettingen, 1997, Germany.
35. Crist D.R., Jordan G.J., Moore D.W., Hashmal J.A., Borsetti A.P., and Turujman S.A. J. Am. Chem. Soc. 105 (1983) 4136-4142
36. Taylor E.C., and Sobieray D.M. Tetrahedron 47 (1991) 9598-9620
37. Shamma M., and Tomlinson H.H. J. Org. Chem. 43 (1978) 1852-2855
38. Flack H.D. Acta Crystallogr., Sect. A 39 (1983) 876-881
39. Fieser L.F., and Fieser M. Reagents for Organic Synthesis Vol. 6 (1967), John Wiley & Sons, New York; London 34-35
40. Venkov A.P., and Ivanov I.I. Tetrahedron 52 (1996) 12299-12308
41. Orito K., Matsuzaki T., Suginome H., and Rodrigo R. Heterocycles 27 (1988) 2403-2412
42. Brossi A., Dolan L.A., and Teitel S. Org. Synth. 56 (1977) 3
43. Le Quang N.T., and Gardent J. Bull. Soc. Chim. Fr. 5 (1966) 2401
44. Yamamoto M., Hashigaki K., Qais N., and Ishikawa S. Tetraheron 46 (1990) 5909-5920
45. Wanner K.Th., Praschak J., and Nagel U. Arch. Pharm. 323 (1990) 335-350
46. Polniaszek R.P., and Kaufman C.R. J. Am. Chem. Soc. 111 (1989) 4859-4863