Efficient stereoselective synthesis of enantiopure 2-substituted paraconic acids

Tetrahedron Asymmetry

Volumn 19, Issue 8, 2008, Pages 896-899

  Kim, Hyun Chul ^a   Park, Oee Sook ^a  

^a Chungbuk National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 OXOTETRAHYDROFURAN 3 CARBOXYLIC ACID; ALDEHYDE; CARBOXYLIC ACID DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE; N ACYL OXAZOLIDINONE; OXAZOLIDINONE DERIVATIVE; PARACONIC ACID;

ALDOL REACTION; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 43149086354     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.02.031     Document Type: Article

References (19)

1. Zopf W. Liebigs Ann. Chem. 324 (1902) 39
2. Jacobi P.A., and Herradura P. Tetrahedron Lett. 37 (1996) 8297
3. Sibi M.P., Deshpande P.K., and La Loggia A.J. Synlett 343 (1996) and references cited therein
4. Thurston L.S., Imakyura Y., Haruna M., Li D.H., Liu Z.C., Liu S.Y., Cheng Y.C., and Lee K.H. J. Med. Chem. 32 (1989) 604
5. Tomioka K., Kubota Y., Kawasaki H., and Koga K. Tetrahedron Lett. 30 (1989) 2949
6. Berti F., Felluga F., Forzato C., Furlan G., Nitti P., Pitacco G., and Valentin E. Tetrahedron: Asymmetry 17 (2006) 2344
7. Chhor R.B., Nosse B., Sorgel S., Bohm C., Seitz M., and Reiser O. Chem. Eur. J. 9 (2003) 260
8. Selvakumar N., Kumar P.K., Reddy S.K.C., and Chary B.C. Tetrahedron Lett. 48 (2007) 2021
9. Sibi M.P., Liu P., Ji J., Hajra S., and Chen J. J. Org. Chem. 67 (2002) 1738
10. Barros M.T., Maycock C.D., and Ventra M.R. Org. Lett. 5 (2003) 4097
11. Lawlor J.M., and McNamee M.B. Tetrahedron Lett. 24 (1983) 2211
12. Gage J.R., and Evans D.A. Org. Synth. 68 (1990) 77
13. Evans D.A., Bartroli J., and Shih T.L. J. Am. Chem. Soc. 103 (1981) 2127
14. Evans D.A., Rieger D.L., Bilodeau M.T., and Urpi F. J. Am. Chem. Soc. 114 (1991) 1047
15. Van Horn D.E., and Masamune S. Tetrahedron Lett. 24 (1979) 2229
16. Yan T.H., Tan C.W., Lee H.C., Lo H.C., and Huang T.Y. J. Am. Chem. Soc. 115 (1993) 2613
17. 18 symmetry reverse phase column that contains 5 μL packing L1. The flow rate is about 1.0 mL per min, the injection volume is 10.0 μL, and the run time is 20 min, by using 20% acetonitrile and water as a gradient solvent system.
18. Evans D.A., Britton D.C., and Ellman J.A. Tetrahedron Lett. 28 (1987) 6141
19. Kim, H. C.; Park, O. S., in preparation.