A β-Lactone route to chiral γ-substituted α-amino acids: Application to the concise synthesis of (S)-α-azidobutyro lactone and a natural amino acid

Organic Letters

Volumn 4, Issue 4, 2002, Pages 533-536

  Tennyson, Reginald L ^a,b   Cortez, Guillermo S ^a   Galicia, Héctor J ^a   Kreiman, Charles R ^a   Thompson, Christina M ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b TEXAS BIOTECHNOLOGY CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALPHA AZIDOBUTYROLACTONE; ALPHA-AZIDOBUTYROLACTONE; AMINO ACID; AZIDE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GAMMA BUTYROLACTONE; LACTONE;

ARTICLE; CHEMISTRY; PLANT; PLANT SEED; SYNTHESIS;

4-BUTYROLACTONE; ALDEHYDES; AMINO ACIDS; AZIDES; INDICATORS AND REAGENTS; LACTONES; PLANTS; SEEDS;

EID: 0037149034     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017120b     Document Type: Article

References (19)

1. (a) For a review describing routes to optically active β-lactones, see: Yang, H. W.; Romo, D. Tetrahedron 1999, 51, 6403-6434.
2. (b) For more recent advances in this area, see: Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742-9743.
3. Tennyson, R. L.; Romo, D. J. Org. Chem. 2000, 65, 7248-7252.
4. Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125-2128.
5. (e) Doyle, M. P.; May, E. J. Synlett 2001, 967-969.
6. (f) Cortez, G. S.; Tennyson, R. L.; Romo, D. J. Am. Chem. Soc. 2001, 123, 7945-7946.
7. (g) Cortez, G. S.; Oh, S. H.; Romo, D. Synthesis 2001, 1731-1736.
8. Both (R)- and (S)-3-hydroxy-4,4,4-trichorobutyric-β-lactone (98% ee) are available from Aldrich ($3.12/g and $3.09/g, respectively, 2000-2001 catalog).
9. Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 1992, 114, 1906-1908.
10. Fowden, L.; MacGibbon, C. M.; Mellon, F. A.; Sheppard, R. C. Phytochem. 1972, 11, 1105-1110.
11. Song, C. E.; Lee, J. K.; Lee, S. H.; Lee, S. Tetrahedron: Asymmetry 1995, 6, 1063-1066.
12. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408-7410.
13. Brown, D. G.; Velthulsend, E. J.; Commerford; Brisbois, R.; Hoye, T. R. J. Org. Chem. 1996, 61, 2540-2541.
14. Both (R)- and (S)-homoserine are available from Aldrich at high cost ($208/g and $50/g, respectively, 2000-2001 catalog).
15. Stachel, S. J.; Lee, C. B.; Spassova, M.; Chappell, M. D.; Bornmann, W. G.; Danishefsky, S. J.; Chou, T.-C.; Guan, Y. J. Org. Chem. 2001, 66, 4369-4378.
16. Cooper, R. D. G.; Jose, F.; McShane, L.; Koppel, G. A. Tetrahedron Lett. 1978, 2243-2246.
17. Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41.
18. For a previous synthesis of optically active azido lactone 7 via resolution, see: Davis, M.; Dudman, N. P. B.; White, H. F. Aust. J. Chem. 1985, 38, 621-624.
19. Fujisawa, T.; Ito, T. Nishiura, S.; Shimizu, M. Tetrahedron Lett. 1998, 39, 9735-9738.