The use of lithium (α-methylbenzyl)allylamide for the asymmetric synthesis of unsaturated β-amino acid derivatives

Tetrahedron Asymmetry

Volumn 8, Issue 20, 1997, Pages 3387-3391

  Davies, Stephen G ^a   Fenwick, David R ^a   Ichihara, Osamu ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b Oxford Asymmetry Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 (N TERT BUTOXYCARBONYL)AMINO 2 HYDROXYHEX 4 ENOIC ACID METHYL ESTER; 3 (N TERT BUTOXYCARBONYL)AMINOHEX 4 ENOATE; AMINO ACID DERIVATIVE; BETA AMINO ACID; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030697229     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00470-9     Document Type: Article

References (28)

1. T. Uyehara, N. Asao and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1987, 1410; J. M. Hawkins and T. A. Lewis, J. Org. Chem., 1994, 59, 649; D. Enders, H. Wahl and W. Bettray, Angew. Chim. Int. Ed. Engl., 1995, 34, 455; M. Shimano and A. I. Meyers, J. Org. Chem., 1995, 60, 7445; J. G. Rico, R. J. Lindmark, T. E. Rogers and P. R. Bovy, J. Org. Chem., 1993, 58, 7948.
2. T. Uyehara, N. Asao and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1987, 1410; J. M. Hawkins and T. A. Lewis, J. Org. Chem., 1994, 59, 649; D. Enders, H. Wahl and W. Bettray, Angew. Chim. Int. Ed. Engl., 1995, 34, 455; M. Shimano and A. I. Meyers, J. Org. Chem., 1995, 60, 7445; J. G. Rico, R. J. Lindmark, T. E. Rogers and P. R. Bovy, J. Org. Chem., 1993, 58, 7948.
3. T. Uyehara, N. Asao and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1987, 1410; J. M. Hawkins and T. A. Lewis, J. Org. Chem., 1994, 59, 649; D. Enders, H. Wahl and W. Bettray, Angew. Chim. Int. Ed. Engl., 1995, 34, 455; M. Shimano and A. I. Meyers, J. Org. Chem., 1995, 60, 7445; J. G. Rico, R. J. Lindmark, T. E. Rogers and P. R. Bovy, J. Org. Chem., 1993, 58, 7948.
4. T. Uyehara, N. Asao and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1987, 1410; J. M. Hawkins and T. A. Lewis, J. Org. Chem., 1994, 59, 649; D. Enders, H. Wahl and W. Bettray, Angew. Chim. Int. Ed. Engl., 1995, 34, 455; M. Shimano and A. I. Meyers, J. Org. Chem., 1995, 60, 7445; J. G. Rico, R. J. Lindmark, T. E. Rogers and P. R. Bovy, J. Org. Chem., 1993, 58, 7948.
5. T. Uyehara, N. Asao and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1987, 1410; J. M. Hawkins and T. A. Lewis, J. Org. Chem., 1994, 59, 649; D. Enders, H. Wahl and W. Bettray, Angew. Chim. Int. Ed. Engl., 1995, 34, 455; M. Shimano and A. I. Meyers, J. Org. Chem., 1995, 60, 7445; J. G. Rico, R. J. Lindmark, T. E. Rogers and P. R. Bovy, J. Org. Chem., 1993, 58, 7948.
6. S. G. Davies and G. D. Smyth, J. Chem. Soc., Perkin Trans. I, 1996, 2467; S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1996, 7, 1919; S. G. Davies and D. J. Dixon, J. Chem. Soc., Chem. Commun., 1996, 1797; S. G. Davies and G. Bhalay, Tetrahedron: Asymmetry, 1996, 7, 1595. Also see reference 4 and papers quoted therein.
7. S. G. Davies and G. D. Smyth, J. Chem. Soc., Perkin Trans. I, 1996, 2467; S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1996, 7, 1919; S. G. Davies and D. J. Dixon, J. Chem. Soc., Chem. Commun., 1996, 1797; S. G. Davies and G. Bhalay, Tetrahedron: Asymmetry, 1996, 7, 1595. Also see reference 4 and papers quoted therein.
8. S. G. Davies and G. D. Smyth, J. Chem. Soc., Perkin Trans. I, 1996, 2467; S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1996, 7, 1919; S. G. Davies and D. J. Dixon, J. Chem. Soc., Chem. Commun., 1996, 1797; S. G. Davies and G. Bhalay, Tetrahedron: Asymmetry, 1996, 7, 1595. Also see reference 4 and papers quoted therein.
9. S. G. Davies and G. D. Smyth, J. Chem. Soc., Perkin Trans. I, 1996, 2467; S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1996, 7, 1919; S. G. Davies and D. J. Dixon, J. Chem. Soc., Chem. Commun., 1996, 1797; S. G. Davies and G. Bhalay, Tetrahedron: Asymmetry, 1996, 7, 1595. Also see reference 4 and papers quoted therein.
10. M. Namikoshi, K. L. Rinehart, A. M. Dahlem, V. R. Beasley and W. W. Carmichael, Tetrahedron Lett., 1989, 30, 4349 and references cited therein.
11. S. G. Davies and D. R. Fenwick, J. Chem. Soc., Chem. Commun., 1995, 1109.
12. S. G. Davies, C. J. R. Hedgecock and J. M. McKenna, Tetrahedron: Asymmetry, 1995, 6, 827; Tetrahedron: Asymmetry, 1995, 6, 2507.
13. S. G. Davies, C. J. R. Hedgecock and J. M. McKenna, Tetrahedron: Asymmetry, 1995, 6, 827; Tetrahedron: Asymmetry, 1995, 6, 2507.
14. S. G. Davies and D. R. Fenwick, J. Chem. Soc., Chem. Commun., 1997, 565.
15. (E,E)-tert-butyl hex-2,4-dienoate 6 was prepared from the commercially available (E,E)-hex-2,4-dienoic acid with isobutylene and a catalytic amount of concentrated sulfuric acid.
16. B. C. Laguzza and B. Ganem, Tetrahedron Lett., 1978, 19, 1689.
17. R. Gigg and P. A. Gent, J. Chem. Soc., Chem. Commun., 1974, 277.
18. S. T. Hodgson, D. M. Hollinshead and S. V. Ley, Tetrahedron, 1985, 41, 5871.
19. J. E. Semple, P. C. Wang, Z. Lysenko and M. M. Joullié, J. Am. Chem. Soc., 1980, 102, 7505.
20. +, 10%), 144 (100%). All other compounds in Scheme 1 exhibited satisfactory spectroscopic and analytical data.
21. M. E. Bunnage, A. N. Chernega, S. G. Davies and C. J. Goodwin, J. Chem. Soc., Perkin Trans. I, 1994, 2373 and references cited therein.
22. F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109.
23. For an analogous cyclisation to a perhydro-1,3-oxazine, see reference 6.
24. S. Futagawa, T. Inui and T. Shiba, Bull. Chem. Soc. Jpn., 1973, 46, 3308; T. M. Williams, R. Crumbie and H. S. Mosher, J. Org. Chem., 1985, 50, 91.
25. S. Futagawa, T. Inui and T. Shiba, Bull. Chem. Soc. Jpn., 1973, 46, 3308; T. M. Williams, R. Crumbie and H. S. Mosher, J. Org. Chem., 1985, 50, 91.
26. Y. Ohfune, P. A. Grieco, C.-L. J. Wang and G. Majetich, J. Am. Chem. Soc., 1978, 100, 5946.
27. T. Ishizuka and T. Kunieda, Tetrahedron Lett., 1987, 28, 4185.
28. 1H NMR spectrum due to restricted rotation about the amide bond, even at 70°C. All other compounds in Scheme 2 exhibited satisfactory spectroscopic and analytical data.