Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

Tetrahedron Asymmetry

Volumn 13, Issue 20, 2002, Pages 2229-2234

  Amedjkouh, Mohamed ^a   Ahlberg, Per ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

(PIPERIDINE 1 CARBONYL)PYRROLIDIN 2 ONE; (PYRROLIDINE 1 CARBONYL)PYRROLIDIN 2 ONE; 2 (N METHYL 1 CARBONYL)PYRROLIDINE 1 CARBALDEHYDE; 2 (PIPERIDINE 1 CARBONYL)PYRROLIDINE 1 CARBALDEHYDE; 2 (PYRROLIDINE 1 CARBONYL)PYRROLIDINE 1 CARBALDEHYDE; 2 TRICHLOROMETHYL 1 AZA 3 OXABICYCLO[3.3.0]OCTAN 4 ONE; 2 TRICHLOROMETHYL 1 AZA 3 OXABICYCLO[3.3.0]OCTAN 4,8 DIONE; 2 TRICHLOROMETHYLOXAZOLIDIN 4 ONE; 5 OXOPYRROLIDINE CARBOXYLIC ACID BENZYLAMIDE; 5 OXOPYRROLIDINE CARBOXYLIC ACID PHENYLETHYLAMIDE; AMIDE; DIAMINE; KETONE DERIVATIVE; N METHYL 2 (1 PIPERIDINYLMETHYL)PYRROLIDINE; N METHYL 2 (1 PYRROLIDINOMETHYL)PYRROLIDINE; PROLINE; PROLYLDIMETHYLAMINE; PROLYLPYRROLIDINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRECURSOR; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SYNTHESIS;

EID: 0037131663     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00579-7     Document Type: Article

References (24)

1. Mukaiyama T. Tetrahedron. 37:1981;4111-4119.
2. Mukaiyama T., Asami M. Topics in Current Chemistry. 127:1985;133-167 Springer-Verlag, Berlin.
3. Asami M. Bull. Chem. Soc. Jpn. 63:1990;721-727.
4. Asami M., Watanabe H., Honda K., Inoue S. Tetrahedron: Asymmetry. 9:1998;4165-4173.
5. Asami M., Inoue S. Bull. Chem. Soc. Jpn. 70:1997;1687-1690.
6. Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455-1460.
7. Colombo L., Gennari C., Poli G., Scolastico C. Tetrahedron. 38:1982;2725-2727.
8. Corey E.J., Hannon F.J. Tetrahedron Lett. 28:1987;5233-5236.
9. Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T. J. Am. Chem. Soc. 113:1991;4247-4252.
10. Kobayashi S., Koribe M. Chem. Eur. J. 3:1997;1472-1481.
11. Betancort J.M., Barbas C.F. III. Org. Lett. 3:2001;3737-3740.
12. Denmark S.E., Su X., Nishigaichi Y., Coe D.M., Wong K.-T., Winter S.B.D., Choi J.Y. J. Org. Chem. 64:1999;1958-1967.
13. Brunel J.M., Hilermann M.-H., Heumann A., Buono G. Chem. Commun. 2000;1869-1870.
14. Brunel J.M., Constantieux T., Buono G. J. Org. Chem. 64:1999;8940-8942.
15. Brunel J.M., Faure B. Tetrahedron: Asymmetry. 6:1995;2353.
16. Hendrie S.K., Leonard J. Tetrahedron. 14:1987;3289.
17. de Sousa S.E., O'Brien P., Poumellec P. J. Chem. Soc., Perkin Trans. 1. 1998;1483-1492.
18. Alker D., Doyle K.J., Harwood L.M., McGregor A. Tetrahedron: Asymmetry. 1:1990;877-880.
19. Harrison J.R., O'Brien P. Synth. Commun. 31:2001;1155-1160.
20. Orsini F., Pelizzoni F., Forte M., Sisti M., Bombieri G., Benetollo F. J. Heterocyclic Chem. 26:1989;837-841.
21. Polonski T. Tetrahedron. 41:1985;603.
22. Dane E., Heiss R., Shafer H. Angew. Chem. 71:1959;339.
23. Angier S. J. Org. Chem. 21:1956;1540-1542.
24. Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T. J. Am. Chem. Soc. 113:1991;4247.