Highlights of the Chemistry of Enantiomerically Pure Aziridine-2- carboxylates

Aldrichimica Acta

Volumn 36, Issue 2, 2003, Pages 57-63

  Lee, Won Koo ^a   Ha, Hyun Joon ^b  

^a Sogang University   (South Korea)

^b Hankuk University of Foreign Studies   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; REVIEW; RING OPENING; STEREOCHEMISTRY;

EID: 0344153361     PISSN: 00025100     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (45)

1. (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247 and references therein.
2. (b) Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Synthesis III; Metz, P., Ed.; Topics in Current Chemistry Series 216; Springer-Verlag: Berlin, 2001; Vol. 216, pp 93-124.
3. (c) M'Coull, W.; Davis, F. A. Synthesis 2000, 1347.
4. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
5. (e) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: New York, 1996; Vol. 1A, p 1.
6. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
7. Baldwin, J. E.; Farthing, C. N.; Russell, A. T.; Schofield, C. J.; Spivey, A. C. Tetrahedron Lett. 1996, 37, 3761.
8. Garner, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 1994, 35, 1653.
9. Cardillo, G.; Gentilucci, L.; Tomasini, C.; Visa Castejon-Bordas, M. P. Tetrahedron: Asymmetry 1996, 7, 755.
10. Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676.
11. McLaren, A. B.; Sweeney, J. B. Org. Lett. 1999, 1, 1339.
12. Aires-de-Sousa, J.; Lobo, A. M.; Prabhakar, S. Tetrahedron Lett. 1996, 37, 3183.
13. Alezra, V.; Bouchet, C.; Micouin, L.; Bonin, M.; Husson, H.-P. Tetrahedron Lett. 2000, 41, 655.
14. Martres, M.; Gil, G.; Méou, A. Tetrahedron Lett. 1994, 35, 8787.
15. Lee, W. K.; Ha, H.-J. Sogang University and Hankuk University of Foreign Studies, Seoul and Yongin, Korea. Unpublished results, 2002.
16. Lee, W. K.; Lim, Y.; Ha, H.-J. Kor. Pat. Appl. No. 10-20000-0046387, 2000.
17. (a) De Jonghe, S.; Lamote, I.; Venkataraman, K.; Boldin, S. A.; Hillaert, U.; Rozenski, J.; Hendrix, C.; Busson, R.; De Keukeleire, D.; Van Calenbergh, S.; Futerman, A. H.; Herdewijn, P. J. Org. Chem. 2002, 67, 988.
18. (b) Lee, E.; Song, H. Y.; Kang, J. W.; Kim, D.-S.; Jung, C.-K.; Joo, J. M. J. Am. Chem. Soc. 2002, 124, 384 .
19. Park, C. S.; Choi, H. G.; Lee, H.; Lee, W. K.; Ha, H.-J. Tetrahedron: Asymmetry 2000, 11, 3283.
20. Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075.
21. Hwang, G.-I.; Chung, J.-H.; Lee, W. K. J. Org. Chem. 1996, 61, 6183.
22. (a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
23. (b) Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
24. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
25. Kim, B. C.; Lee, W. K. Tetrahedron 1996, 52, 12117.
26. Lee, W. K.; Ha, H.-J. Sogang University and Hankuk University of Foreign Studies, Seoul and Yongin, Korea. Unpublished results, 2003.
27. Lee, W. K.; Ha, H.-J. Sogang University and Hankuk University of Foreign Studies, Seoul and Yongin, Korea. Unpublished results, 2002.
28. The absolute configuration of the new stereogenic center was determined after regioselective ring opening followed by cyclic urea formation.
29. Wadsworth, W. S., Jr. Org. React. 1977, 25, 73.
30. Lim, Y.; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431.
31. Choi, S.-K.; Lee, J.-S.; Kim, J.-H.; Lee, W. K. J. Org. Chem. 1997, 62, 743.
32. Choi, S.-K.; Lee, W. K. Heterocycles 1998, 48, 1917.
33. Bae, J. H.; Shin, S.-H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041.
34. Shin, S.-H.; Han, E. Y.; Park, C. S.; Lee, W. K.; Ha, H.-J. Tetrahedron: Asymmetry 2000, 11, 3293.
35. For other selected approaches to chiral oxazolidinones, see: (a) Lucarini, S.; Tomasini, C. J. Org. Chem. 2001, 66, 727. (b) Benedetti, F.; Norbedo, S. Tetrahedron Lett. 2000, 41, 10071. (c) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (d) Bach, T.; Schröder, J. Tetrahedron Lett. 1997, 38, 3707. (e) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A.; Rowe, C. G. Tetrahedron Lett. 1994, 35, 5409.
36. For other selected approaches to chiral oxazolidinones, see: (a) Lucarini, S.; Tomasini, C. J. Org. Chem. 2001, 66, 727. (b) Benedetti, F.; Norbedo, S. Tetrahedron Lett. 2000, 41, 10071. (c) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (d) Bach, T.; Schröder, J. Tetrahedron Lett. 1997, 38, 3707. (e) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A.; Rowe, C. G. Tetrahedron Lett. 1994, 35, 5409.
37. For other selected approaches to chiral oxazolidinones, see: (a) Lucarini, S.; Tomasini, C. J. Org. Chem. 2001, 66, 727. (b) Benedetti, F.; Norbedo, S. Tetrahedron Lett. 2000, 41, 10071. (c) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (d) Bach, T.; Schröder, J. Tetrahedron Lett. 1997, 38, 3707. (e) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A.; Rowe, C. G. Tetrahedron Lett. 1994, 35, 5409.
38. For other selected approaches to chiral oxazolidinones, see: (a) Lucarini, S.; Tomasini, C. J. Org. Chem. 2001, 66, 727. (b) Benedetti, F.; Norbedo, S. Tetrahedron Lett. 2000, 41, 10071. (c) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (d) Bach, T.; Schröder, J. Tetrahedron Lett. 1997, 38, 3707. (e) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A.; Rowe, C. G. Tetrahedron Lett. 1994, 35, 5409.
39. For other selected approaches to chiral oxazolidinones, see: (a) Lucarini, S.; Tomasini, C. J. Org. Chem. 2001, 66, 727. (b) Benedetti, F.; Norbedo, S. Tetrahedron Lett. 2000, 41, 10071. (c) Tomasini, C.; Vecchione, A. Org. Lett. 1999, 1, 2153. (d) Bach, T.; Schröder, J. Tetrahedron Lett. 1997, 38, 3707. (e) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A.; Rowe, C. G. Tetrahedron Lett. 1994, 35, 5409.
40. Sim, T. B.; Kang, S. H.; Lee, K. S.; Lee, W. K.; Yun, H.; Dong, Y.; Ha, H.-J. J. Org. Chem. 2003, 68, 104.
41. Park, C. S.; Kim, M. S.; Sim, T. B.; Pyun, D. K.; Lee, C. H.; Choi, D.; Lee, W. K.; Chang, J.-W.; Ha, H.-J. J. Org. Chem. 2003, 68, 43.
42. Cardillo, G.; Orena, M.; Sandri, S. J. Org. Chem. 1986, 51, 713.
43. Chang, J.-W.; Bae, J. H.; Shin, S.-H.; Park, C. S.; Choi, D.; Lee, W. K. Tetrahedron Lett. 1998, 39, 9193.
44. Chang, J.-W.; Ha, H.-J.; Park, C. S.; Kim, M. S.; Lee, W. K. Heterocycles 2002, 57, 1143.
45. Available from Sigma-Aldrich Co. (www.sigma-aldrich.com) and Imagene (www.imagene.co.kr).