Asymmetric synthesis of β-substituted α-amino acids using 2H-azirine-2-carboxylate esters. Synthesis of 3,3-disubstituted aziridine-2-carboxylate esters

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3796-3797

  Davis, Franklin A ^a   Liang, Chang Hsing ^a   Liu, Hu ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZIRIDINECARBOXYLIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030851227     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9702610     Document Type: Article

References (32)

1. (a) Yoshioka, H.; Aoki, T.; Goko, H.; Nakatsu, K.; Noda, T.; Sakakibara, H.; Take, T.; Nagata, A.; Abe, J.; Wakamiya, T.; Shiba, T.; Kaneko, T. Tetrahedron Lett. 1971, 2043.
2. (b) Takita, T.; Muraola, Y.; Yoshioka, T.; Fuji, A.; Naeda, K.; Umezawa, H. J. Antibiot. 1972, 25, 755.
3. (c) Barrett, G. C. Amino Acids, Peptides and Proteins; The Chemical Society: London, 1980; Vol. 13, p 1.
4. For leading references see: (a) Kazmierski W. M.; Yamamura, H. I.; Hruby, V. J. J. Am. Chem. Soc. 1991, 113, 2275. (b) Holladay, M. W.; Nadzan, A. M. J. Org. Chem. 1991, 56, 3900. (c) Kamierski, W. M.; Urbanczyk-Lipkowska, Z.; Hruby, V. J. J. Org. Chem. 1994, 59, 1789.
5. For leading references see: (a) Kazmierski W. M.; Yamamura, H. I.; Hruby, V. J. J. Am. Chem. Soc. 1991, 113, 2275. (b) Holladay, M. W.; Nadzan, A. M. J. Org. Chem. 1991, 56, 3900. (c) Kamierski, W. M.; Urbanczyk-Lipkowska, Z.; Hruby, V. J. J. Org. Chem. 1994, 59, 1789.
6. For leading references see: (a) Kazmierski W. M.; Yamamura, H. I.; Hruby, V. J. J. Am. Chem. Soc. 1991, 113, 2275. (b) Holladay, M. W.; Nadzan, A. M. J. Org. Chem. 1991, 56, 3900. (c) Kamierski, W. M.; Urbanczyk-Lipkowska, Z.; Hruby, V. J. J. Org. Chem. 1994, 59, 1789.
7. Nicolas, E.; Russell, K. C.; Knollenberg, J.; Hruby, V. J. J. Org. Chem. 1993, 58, 7565.
8. Oppolzer, W.; Tamura, O.; Deerberg, J. Helv. Chim. Acta 1992, 75, 1965.
9. Shapiro, G.; Buechler, D.; Marzi, M.; Schmidt, K.; Gomez-Lor, B. J. Org. Chem. 1995, 60, 4978.
10. Sibi, M. P.; Deshpande, P. K.; LaLoggia, A. J.; Christensen, J. W. Tetrahedron Lett. 1995, 36, 8961.
11. (a) Belokon, Y. N.; Sagyan, A. S.; Djamgaryan, S. M. Bakhmutov, V. I.; Belikov, V. M. Tetrahedron 1988, 44, 5507.
12. (b) Hanessian, S.; Yang, R.-Y.; Tetrahedron Lett. 1996, 37, 5273.
13. For a review on optically active aziridines see: Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
14. For leading references to optically active aziridine-2-carboxylic acids see: Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243.
15. (a) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J.; Sweeney, J. B. Tetrahedron 1993, 45, 6309 and references cited therein.
16. (b) Legters, J.; Willems, J. G. H.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 59.
17. Tanner, D.; Birgersson, C.; Dhaliwa, H. K. Tetrahedron Lett. 1990, 31, 1903. Church, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151. Lim, Y.; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431. Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035.
18. Tanner, D.; Birgersson, C.; Dhaliwa, H. K. Tetrahedron Lett. 1990, 31, 1903. Church, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151. Lim, Y.; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431. Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035.
19. Tanner, D.; Birgersson, C.; Dhaliwa, H. K. Tetrahedron Lett. 1990, 31, 1903. Church, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151. Lim, Y.; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431. Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035.
20. Tanner, D.; Birgersson, C.; Dhaliwa, H. K. Tetrahedron Lett. 1990, 31, 1903. Church, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151. Lim, Y.; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431. Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035.
21. Davis, F. A.; Liu, H.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 5473.
22. Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525.
23. Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349.
24. Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651.
25. N-Sulfonylaziridines were prepared as previously described. See refs 12 and 13.
26. 3).
27. Carlson, R. M.; Lee, S. Y. Tetrahedron Lett. 1969, 4001 and references cited therein.
28. Kataoka, Y.; Seto, Y.; Yamamoto, M.; Yamada, T.; Kuwata, S.; Wantanabe, H. Bull. Chem. Soc. Jpn. 1976, 49, 1081.
29. Dharanipragada, R.; VanHulle, K.; Bannister, A.; Bear, S.; Kennedy, L.; Hruby, V. J. Tetrahedron 1992, 48, 4733.
30. Mitsui, S.; Sugi, Y. Tetrahedron Lett. 1969, 1287. Mitsui, S.; Sugi, Y. Tetrahedron Lett. 1969, 1291.
31. Mitsui, S.; Sugi, Y. Tetrahedron Lett. 1969, 1287. Mitsui, S.; Sugi, Y. Tetrahedron Lett. 1969, 1291.
32. For the synthesis of unsymmetrical 3,3-disubstituted N-amidoaziridine-2-carboxylic acids see: Hogale, M. B.; Chavan, P. B. Indian J. Chem. B 1993, 581.