Asymmetric Synthesis of α-Amino Acids by Copper-Catalyzed Conjugate Addition of Grignard Reagents to Optically Active Carbamatoacrylates

Journal of the American Chemical Society

Volumn 116, Issue 18, 1994, Pages 8126-8132

  Lander, Peter A ^a   Hegedus, Louis S ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CARBAMIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0027972828     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00097a020     Document Type: Article

References (45)

1. Montgomery, J.; Wieber, G. R.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 6255. For a recent "classical" synthesis of the parent compound by pyrolysis, see: Tamura, 0.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Akiba, T.; Terashima, S. Tetrahedron Lett. 1992, 33, 3487.
2. Wieber, G. M.; Hegedus, L. S.; Akermark, B.; Michaelson, E. J. Org. Chem. 1989, 54, 4649.
3. Masters, J. J.; Hegedus, L. S.; Tamariz, J. J. Org. Chem. 1991, 56, 5666.
4. Masters, J. J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 4547.
5. Hegedus, L. S.; Bates, R. W.; Söderberg, B. C. J. Am. Chem. Soc. 1991, 113, 923.
6. Miller, M. W.; Hegedus, L. S. J. Org. Chem. 1993, 58, 6779.
7. Hegedus, L. S.; deWeck, G.; D'Andrea, S. J. Am. Chem. Soc. 1988, 110, 2122.
8. Hegedus, L. S.; Schwindt, M. A.; DeLombaert, S.; Imwinkelried, R. J. Am. Chem. Soc. 1990, 112, 2264.
9. Hegedus, L. S.; Lastra, E.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1992, 114, 2991.
10. Vernier, J. M.; Hegedus, L. S.; Miller, D. G. J. Org. Chem. 1992, 57, 914.
11. Lastra, E.; Hegedus, L.S. J. Am. Chem. Soc. 1993, 115, 87.
12. Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918.
13. Miller, J. R.; Pulley, S. R.; Hegedus, L. S.; DeLombaert, S. J. Am. Chem. Soc. 1992, 114, 5602.
14. Pulley, S. R.; Hegedus, L. S. J. Am. Chem. Soc. 1993, 115, 9037.
15. Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: London, 1985.
16. Wagner, I.; Musso, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 816.
17. For an excellent monograph, see: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Ed.; Organic Chemistry Series; Pergamon Press: Oxford, U.K., 1989.
18. Williams, R. M.; Im, M.-N. J. Am. Chem. Soc. 1991, 113, 9276 and references therein
19. Williams, R. M.; Hendrix, J. A. J. Org. Chem. 1990, 55, 3723.
20. Schickli, C. P.; Seebach, D. LiebigsAnn. Chem. 1991, 655.
21. Seebach,D.; Bürger,H. M.; Schickli, C. P. LiebigsAnn. Chem. 1991, 669.
22. Groth, U.; Halfbrodt, W.; Schöllkopf, U. Liebigs Ann. Chem. 1992, 351.
23. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125 and references cited therein.
24. Arnold, L. D.; Drover, J. C. G.; Vederas, J. C. J. Am. Chem. Soc. 1987, 109, 4649.
25. Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397.
26. Cyclopropanation: (a) Williams, R. M.; Fegley, G. J. J. Org. Chem. 1993, 58, 6933.
27. Williams, R. M.; Fegley, G. J. J. Am. Chem. Soc. 1991, 113, 8796. [3 + 2] cycloaddition: Williams, R. M.; Fegley, G. Tetrahedron Lett. 1992, 33, 6755.
28. Pfammatter, E.; Seebach, D. Liebigs Ann. Chem. 1991, 1323.
29. Beckwith, A. L. J.; Chai, C. L. L. J. Chem. Soc., Chem. Commun. 1990, 1087.
30. Belokon, Y. N.; Sagyan, A. S.; Djamgaryan, S. M.; Bakhmutov, V. I.; Belikov, V. M. Tetrahedron 1988, 44, 5507.
31. Labia, R.; Morin, C. J. Org. Chem. 1986, 57, 249.
32. Baldwin, J. E.; Holfe, G. A.; Lever, O. W., Jr. J. Am. Chem. Soc. 1974, 96, 7125.
33. O-vinyl carbamates; Sengupta, S.; Snieckus, V. J. Org. Chem. 1990, 55, 5680.
34. Enamines: Boeckman, R. K.; Walters, M. A.; Koyano, H. Tetrahedron Lett. 1989, 30, 4787.
35. For a related process using mercuric chloride as the trapping agent, see: Eaton, P. A.; Daniels, R. G.; Casucci, P.; Cunkle, G. T. J. Org. Chem. 1987, 52, 2100. We thank Prof. V. Snieckus for suggesting this approach.
36. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
37. For copper-catalyzed conjugate additions to achiral acetamidoacrylates, see: Cardellichio, C.; Frandance, V.; Marchese, G.; Naso, F.; Ronzini, L. Tetrahedron Lett. 1985, 26, 4387.
38. For a comprehensive review of copper-catalyzed Grignard reactions, see: Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
39. Naphthalenes substituted in the 1-position are preferentially reduced at the substituted ring: Rylander, P. N. Hydrogénation Methods; Academic Press: New York, 1985; p 120.
40. Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Can. J. Chem. 1992, 70, 2325.
41. Cativieles, C.; Lopez, M. P.; Majorai, J. A. Synlett 1992, 21.
42. Dieter, K. R.; Silks, L. A.; Fishpaugh, J. R.; Kastner, M. E. Am. Chem. Soc. 1985, 107, 4679.
43. Fitton, P.; M'Keon, J.E.; Beau, B.C. J. Chem.Soc, Chem. Commun. 1969, 370.
44. Molle, J.; Bauer, P.; Dubois, J. E. J. Org. Chem. 1982, 47, 4120.
45. Oppolzer, W.; Moretti, R. Tetrahedron 1988, 44, 5541.