A general method for the synthesis of enantiomerically pure β- substituted, β-amino acids through α-substituted succinic acid derivatives

Journal of Organic Chemistry

Volumn 64, Issue 17, 1999, Pages 6411-6417

  Evans, David A ^a   Wu, Leester D ^a   Wiener, John J M ^a   Johnson, Jeffrey S ^a   Ripin, David H B ^a   Tedrow, Jason S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BETA AMINO ACID; CARBOXYLIC ACID; SUCCINIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; ENANTIOMER; HYDROLYSIS; SYNTHESIS;

EID: 0033588390     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990756k     Document Type: Article

References (40)

1. Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855-78 and references therein.
2. Juaristi, E.; Quintana, D.; Escalante J. Aldrichim. Acta 1994, 27, 3-11 and references therein.
3. For example: Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117-128.
4. For reviews, see: (a) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997. (b) Cole, D. C. Tetrahedron 1994, 32, 9517-9582. (c) Reference 2. (d) Reference 3.
5. For reviews, see: (a) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997. (b) Cole, D. C. Tetrahedron 1994, 32, 9517-9582. (c) Reference 2. (d) Reference 3.
6. For reviews, see: (a) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997. (b) Cole, D. C. Tetrahedron 1994, 32, 9517-9582. (c) Reference 2. (d) Reference 3.
7. For reviews, see: (a) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997. (b) Cole, D. C. Tetrahedron 1994, 32, 9517-9582. (c) Reference 2. (d) Reference 3.
8. Hawkins, J. M.; Fu, G. C. J. Org. Chem. 1986, 51, 2820-2822.
9. For example: Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183-186.
10. d'Angelo, J.; Maddaluno, J. J. Am. Chem. Soc. 1986, 108, 8112-8114.
11. Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trerè, A. J. Org. Chem. 1993, 58, 5615-5619.
12. Juaristi, E.; Quintana D.; Lamatsch, B.; Seebach, D. J. Org. Chem. 1991, 56, 2553-2557.
13. Evans, D. A.; Urpí, F.; Sommers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215-8216.
14. Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872.
15. Kim, B. J.; Park, Y. S.; Beak, P. J. Org. Chem. 1999, 64, 1705-1708.
16. Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164.
17. Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615-6616.
18. Evans, D. A.; Kim, A. S. In Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A., Ed.; Wiley & Sons: New York, 1995; Vol. 1, pp 345-356.
19. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
20. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144.
21. Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 83-91.
22. Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525-5540.
23. Diastereoselective alkylation of a chiral imide enolate with bromoacetate esters is precedented; see ref 16 and the following: Beckett, R. P.; Crimmin, M. J.; Davis, M. H.; Spavold, Z. Synlett 1993, 137-138.
24. Rosencranz, G.; Mancera, O.; Gatica, J.; Djerassi, C. J. Am. Chem. Soc. 1950, 73, 4077-4080.
25. (a) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030.
26. (b) Evans, D. A.; Britton, T. C.; Dellaria, J. F., Jr. Tetrahedron 1988, 44, 5525-5540.
27. (c) Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346-4348.
28. Heathcock, C. H. Aldrichim. Acta 1990, 23, 99-111.
29. (b) Heathcock, C. H.; Flippin, L. A. J. Am. Chem. Soc. 1983, 105, 1667-1668.
30. (a) Damon, R. E.; Coppola, G. M. Tetrahedron Lett. 1990, 31, 2849-2852.
31. (b) Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497-4513.
32. (c) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786-787.
33. (a) Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151-2157.
34. (b) Bower, J. F.; Jumnah, R.; Williams, A. C.; Williams, J. M. J. J. Chem. Soc., Perkin Trans 1 1997, 1411-1420.
35. Jacobi, P. A.; Murphree, S.; Rupprecht, F.; Zheng, W. J. Org. Chem. 1996, 61, 2413-2427.
36. Isocyanate formation was monitored by infrared spectroscopy.
37. Yakushijin, K.; Kozuka, M.; Morishita, T.; Furukawa, H. Chem. Pharm. Bull. 1981, 29, 2420-2430.
38. Sato, M.; Tatsuno, T. Chem. Pharm. Bull. 1968, 16, 2182-2190.
39. Buchschacher, P.; Cassal, J.-M.; Fürst, A.; Meier, W. Helv. Chim. Acta 1977, 60, 2747-2755.
40. Okamoto, S.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1979, 52, 2670-2673.