Stereocontrolled synthesis of anti-α-hydroxy-β-amino and anti-α,β-diamino acid derivatives by epoxidation of 1-arylthio-1-nitroalkenes

Synthesis

Volumn , Issue 15, 2002, Pages 2296-2308

  Ambroise, Lydia ^a,b   Dumez, Estelle ^a,b   Szeki, Andrea ^a,b   Jackson, Richard F W ^a,b  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

Amino acids; Amino aldehydes; Epoxidation; Epoxides; Stereoselective synthesis

Indexed keywords

AMINO ACIDS; AMMONIA; DERIVATIVES; OLEFINS;

EPOXIDATION;

STEREOCHEMISTRY;

ALDEHYDE; ALKENE; AMINO ACID DERIVATIVE; AMMONIA; BENZYLAMINE; CARBAMIC ACID; EPOXIDE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0036414430     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34851     Document Type: Article

References (50)

1. Enantioselective Synthesis of β-Amino Acids, Juaristi E.; Wiley-VCH: New York, 1997.
2. Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983.
3. Bunnage, M. E.; Chernega, A. N.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. I 1994, 2373.
4. Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. I 1994, 2385.
5. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181.
6. Andruszkiewicz, R. Pol. J. Chem. 1998, 72, 1.
7. Seki, M.; Matsumoto, K. Synthesis 1999, 924.
8. Ha, H. J.; Ahn, Y. G.; Lee, G. S. Tetrahedron: Asymmetry 1999, 10, 2327.
9. Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron: Asymmetry 2001, 12, 347.
10. Bunnage, M. E.; Davies, S. G.; Goodwin, C. J.; Ichihara, O. Tetrahedron 1994, 50, 2975.
11. Li, G. G.; Chang, H. T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
12. Schlingloff, G.; Sharpless, K. B. In Asymmetric Oxidation Reactions; Katsuki, T., Ed.; OUP: Oxford, 2001, 104.
13. Li, G. G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649.
14. Wang, M.; Gould, S. J. J. Org. Chem. 1993, 58, 5176.
15. Greenlee, W. J.; Allibone, P. L.; Perlow, D. S.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1985, 28, 434.
16. Nakamura, Y.; Hirai, M.; Tamotsu, K.; Yonezawa, Y.; Shin, C. G. Bull. Chem. Soc. Jpn. 1995, 68, 1369.
17. Schmidt, U.; Mundinger, K.; Riedl, B.; Haas, G.; Lau, R. Synthesis 1992, 1201.
18. Dunn, P. J.; Häner, R.; Rapoport, H. J. Org. Chem. 1990, 55, 5017.
19. Palomo, C.; Aizpurua, J. M.; Cabre, F.; Cuevas, C.; Munt, S.; Odriozola, J. M. Tetrahedron Lett. 1994, 35, 2725.
20. Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. J. Chem. Soc., Chem. Commun. 1996, 633.
21. Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813.
22. Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629.
23. Burke, A. J.; Davies, S. G.; Hedgecock, C. J. R. Synlett 1996, 621.
24. Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475.
25. Hart, H. S.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045.
26. Zhou, X. T.; Lin, Y. R.; Dai, L. X. Tetrahedron: Asymmetry 1999, 10, 855.
27. Lee, S. H.; Yoon, J.; Chung, S. H.; Lee, Y. S. Tetrahedron 2001, 57, 2139.
28. Luo, Y.; Blaskovich, M. A.; Lajoie, G. A. J. Org. Chem. 1999, 64, 6106.
29. Herranz, R.; Vinuesa, S.; Castro-Pichel, J.; Pérez, C.; García-López, M. T. J. Chem. Soc., Perkin Trans. I 1992, 1825.
30. Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431.
31. Adams, Z. M.; Jackson, R. F. W.; Palmer, N. J.; Rami, H. K.; Wythes, M. J. J. Chem. Soc. Perkin Trans. I 1999, 937.
32. Ambroise, L.; Jackson, R. F. W. Tetrahedron Lett. 1996, 37, 2311.
33. Dumez, E.; Szeki, A.; Jackson, R. F. W. Synlett 2001, 1214.
34. Miyashita, M.; Kumazawa, T.; Yoshikoshi, A. J. Org. Chem. 1980, 45, 2945.
35. Barrett, A. G. M.; Graboski, G. G.; Russell, M. A. J. Org. Chem. 1986, 51, 1012.
36. Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
37. Lehr, F.; Gonnermann, J.; Seebach, D. Helv. Chim. Acta 1979, 62, 2258.
38. Colvin, E. W.; Beck, A. K.; Seebach, D. Helv. Chim. Acta 1981, 64, 2264.
39. Meth-Cohn, O.; Moore, C.; Taljaard, H. C. J. Chem. Soc., Perkin Trans. I 1988, 2663.
40. Wolf, J. P.; Pfander, H. Helv. Chim. Acta 1987, 70, 116.
41. Melon, D.; Gravier-Pelletier, C.; Le Merrer, Y.; Depezay, J. C. Bull. Soc. Chim. Fr. 1992, 129, 585.
42. Full details of the X-ray structures may be found as follows: (a) 13a: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 758. (b) 13b: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 763. (c) 13c: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 760. (d) 18: Clegg, W.; Horsburgh, L. Acta Crystallogr., Sect. E 2002, 58, 767. (e) 23: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 765.
43. Full details of the X-ray structures may be found as follows: (a) 13a: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 758. (b) 13b: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 763. (c) 13c: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 760. (d) 18: Clegg, W.; Horsburgh, L. Acta Crystallogr., Sect. E 2002, 58, 767. (e) 23: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 765.
44. Full details of the X-ray structures may be found as follows: (a) 13a: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 758. (b) 13b: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 763. (c) 13c: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 760. (d) 18: Clegg, W.; Horsburgh, L. Acta Crystallogr., Sect. E 2002, 58, 767. (e) 23: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 765.
45. Full details of the X-ray structures may be found as follows: (a) 13a: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 758. (b) 13b: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 763. (c) 13c: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 760. (d) 18: Clegg, W.; Horsburgh, L. Acta Crystallogr., Sect. E 2002, 58, 767. (e) 23: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 765.
46. Full details of the X-ray structures may be found as follows: (a) 13a: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 758. (b) 13b: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 763. (c) 13c: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 760. (d) 18: Clegg, W.; Horsburgh, L. Acta Crystallogr., Sect. E 2002, 58, 767. (e) 23: Clegg, W.; Elsegood, M. R. J. Acta Crystallogr., Sect. E 2002, 58, 765.
47. Adam, W.; Hadjiarapoglou, L. Tetrahedron Lett. 1992, 33, 469.
48. Ho, P. T.; Ngu, K.-y. J. Org. Chem. 1993, 58, 2313.
49. Dondoni, A.; Perrone, D.; Merino, P. J. Org. Chem. 1995, 60, 8074.
50. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.