Synthesis of 3,3-dimethylazetidine-2-carboxylic acid and some derivatives

Tetrahedron

Volumn 54, Issue 11, 1998, Pages 2619-2630

  De Kimpe, Norbert ^a   Boeykens, Marc ^a   Tourwé, Dirk ^b  

^a GHENT UNIVERSITY   (Belgium)

^b FREE UNIVERSITY OF BRUSSELS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; AZETIDINE 2 CARBOXYLIC ACID; BORANE DERIVATIVE; ESTER; METHANOL;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REDUCTION;

EID: 0032510411     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00024-6     Document Type: Article

References (66)

1. 1. Yang, S.F.; Hoffman, N.E. Ann. Rev. Plant Physiol. 1984, 35, 155-189.
2. 2. Yang, S.F. in Plant Nitrogen Metabolism, Chapter 8, pp. 263-287, Ed. Poulton, J.E.; Romeo, J.T. and Conn, E.E. Plenum Press : New York, 1989.
3. 3. De Kimpe, N.; Sulmon, P.; Brunet, P. J. Org. Chem. 1990, 55, 5777-5784, and references cited therein.
4. 4. Pirrung, M.C.; McGeehan, G.M. Angew. Chem., 1985, 97, 1074-1075.
5. 5. Pirrung, M.C.; McGeehan, G.M. J. Org. Chem., 1986, 51, 2103-2106.
6. 6. Toshima, H.; Niwayama, Y.; Nagata, H.; Greulich, F.; Ichihara, A. Biosci. Biotech. Biochem. 1993, 57, 1394-1395.
7. 7. Hoffman, N.E.; Yang, S.F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195-199.
8. 8. Charette, A.B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732.
9. 9. Jiménez, J.M.; Rifé, J.; Ortuño, R.M. Tetrahedron Asym. 1996, 7, 537-558.
10. 10. Baldwin, J.E.; Adlington, R.M.; Rawlings, B.J. Tetrahedron Lett., 1985, 26, 481-484.
11. 11. Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett. 1994, 575-583.
12. 12. Wick, L.; Tamm, C.; Boller, T. Helv. Chim. Acta, 1995, 78, 403-410.
13. 13. Pirrung, M.C.; Cao, J.; Chen, J. J. Org. Chem., 1995, 60, 5790-5794.
14. 14. Stammer, C.H. Tetrahedron 1990, 46, 2231-2254, and references cited therein.
15. 15. Burgess, K.; Ho, K.-K.; Pal, B. J. Am. Chem. Soc. 1995, 117, 3808-3819.
16. 16. Mendel, D.; Ellman, J.; Schultz, P.G. J. Am. Chem. Soc. 1993, 115, 4359-4360.
17. 17. Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. 1995, 117, 54-65.
18. 18. Burgess, K.; Ke, C.-Y. J. Org. Chem., 1996, 61, 8627-8631.
19. 19. Moore, J.A.; Ayers, R.S. in "The Chemistry of Heterocyclic Compounds", Ed. Weissenberger A. and Taylor E.C., J. Wiley, New York, 1983, Vol. 42, "Small Ring Heterocycles", Part 2, Ed. A. Hassner.
20. 20. De Kimpe, N. in "Comprehensive Heterocyclic Chemistry - Three- and Four-Membered Rings, with All Fused Systems Containing Four-Membered Rings"; Vol. 1B, Chapter 1.18 "Azetidines, Azetines and Azetes : Monocyclic", p. 507-589. Eds. Padwa A., Katritzky A.R., Rees C.W., Scriven E.F.V., Pergamon, Elsevier, Oxford (1996).
21. 21. a) Sugiura, Y.; Tanaka, H.; Mino, Y.; Ishida, T.; Ota, N.; Inoue, M.; Nomoto, K.; Yoshioka, H.; Takemoto, T. J. Am. Chem. Soc. 1981, 103, 6979.
22. b) Oida, F.; Ota, N.; Mino, Y.; Nomoto, K; Sugiura, Y. J. Am. Chem. Soc. 1989, 111, 3436-3437.
23. c) Noma, M.; Noguchi, M.; Tamaki, E. Tetrahedron Lett. 1971, 2017-2020.
24. d) Ohfune, Y.; Tomita, M.; Nomoto, K. J. Am. Chem. Soc. 1981, 103, 2409.
25. e) Hamada, Y.; Shioiri, T. J. Org. Chem. 1986, 51, 5489-5490.
26. f) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1992, 51, 7917-7920.
27. g) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Asymm. 1992, 3, 1069-1074.
28. h) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1992, 51, 7921-7924.
29. i) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 265-274.
30. j) Shioiri, T.; Hamada, Y.; Matsuura, F. Tetrahedron 1995, 51, 3939-3958.
31. 22. Hanessian, S.; Fu, J.-M; Chiara, J.-L.; Di Fabio, R. Tetrahedron Lett., 1993, 34, 4157-4160.
32. 23. Nielsen, E.; Forlani, G.; Cella, R.; Parisi, B. Plant Sci. 1986, 44, 147; Chem. Abstr. 1986, 105, 112253.
33. 23. Nielsen, E.; Forlani, G.; Cella, R.; Parisi, B. Plant Sci. 1986, 44, 147; Chem. Abstr. 1986, 105, 112253.
34. 24. Fowden, L. Phytochemistry 1991, 30, 3859-3860.
35. 25. Devlin, B.R.J. US Pat. 4560401 (1985); Chem. Abstr. 1986, 105, 42626.
36. 25. Devlin, B.R.J. US Pat. 4560401 (1985); Chem. Abstr. 1986, 105, 42626.
37. 26. Verbrugge, P.A.; De Waal, J. US Pat. 4812581 (1989); Chem. Abstr. 1989, 111, 57527.
38. 26. Verbrugge, P.A.; De Waal, J. US Pat. 4812581 (1989); Chem. Abstr. 1989, 111, 57527.
39. 27. Wood, D.; Mason, R. Eur. Pat. 131435 (1985); Chem. Abstr. 1985, 103, 195984.
40. 27. Wood, D.; Mason, R. Eur. Pat. 131435 (1985); Chem. Abstr. 1985, 103, 195984.
41. 28. B.V. Maatschappij (Shell Int. Res.) Jpn. Kokai 6281367 (1987); Chem. Abstr. 1987, 107, 134187.
42. 28. B.V. Maatschappij (Shell Int. Res.) Jpn. Kokai 6281367 (1987); Chem. Abstr. 1987, 107, 134187.
43. 29. De Nie-Sarink, M.; Mason, R. Eur. Pat. 165636 (1985); Chem. Abstr. 1986, 105, 6400.
44. 29. De Nie-Sarink, M.; Mason, R. Eur. Pat. 165636 (1985); Chem. Abstr. 1986, 105, 6400.
45. 30. De Nie-Sarink, M.; Scholes, G. Eur. Pat. 165637 (1985) ; Chem. Abstr. 1986, 105, 224786.
46. 30. De Nie-Sarink, M.; Scholes, G. Eur. Pat. 165637 (1985) ; Chem. Abstr. 1986, 105, 224786.
47. 31. Kozikowski, A.P.; Wroblewski, J.; Costa, E. Eur. Pat. 299513 (1989); Chem. Abstr. 1989, 111, 7211.
48. 31. Kozikowski, A.P.; Wroblewski, J.; Costa, E. Eur. Pat. 299513 (1989); Chem. Abstr. 1989, 111, 7211.
49. 32. Kozikowski, A.P.; Tuckmantel, W.; Reynolds, I.; Wroblewski, J. J. Med. Chem. 1990, 33, 1561-1571.
50. 33. Blythin, D.J.; Green, M.J.; Lauzon, M.J.R.; Shue, H.-J. J. Org. Chem. 1994, 59, 6098-6100 and references cited therein.
51. 34. a) Masaki, M.; Uehara, M.; Hirate, K.; Isowa, Y.; Sato, Y.; Nakashima, Y. Eur. Pat. Appl. EP 393934, A1 901024; Chem. Abstr. 1990, 114, 164815.
52. 34. a) Masaki, M.; Uehara, M.; Hirate, K.; Isowa, Y.; Sato, Y.; Nakashima, Y. Eur. Pat. Appl. EP 393934, A1 901024; Chem. Abstr. 1990, 114, 164815.
53. b) Zagari, A.; Nemethy, G.; Scheraga, H.A. Biopolymers 1990, 30, 951.
54. c) Zagari, A.; Nemethy, G; Scheraga, H.A. Biopolymers 1990, 30, 961.
55. d) Tsai, F.H.; Overberger, C.G; Zand, R. Biopolymers 1990, 30, 1039.
56. 35. Cromwell, N.H.; Phillips, B. Chem. Rev. 1979, 79, 331-358.
57. 36. Backes, J. in Organische Stickstoffverbindungen III (Houden-Weyl), Band E16c, pp. 729-909, Ed. Klamonn, D., G. Thieme Verlag, Stuttgart, New York (1992).
58. 37. Dureault, A.; Portal, M.; Carreoux, F.; Depezay, J.C. Tetrahedron 1993, 49, 4201-4210.
59. 38. Sulmon, P.; De Kimpe, N.; Schamp, N. Tetrahedron 1988, 44, 3653-3670.
60. 39. Sulmon, P.; De Kimpe, N.; Schamp, N. Tetrahedron 1989, 45, 2937-2955.
61. 40. De Kimpe, N.; Stevens, C. Synthesis 1993, 89-91.
62. 41. Boeykens, M.; De Kimpe, N.; Abbaspour Tehrani, K. J. Org. Chem. 1994, 59, 6973-6985.
63. 42. Fedor, L.R.; Bruice, T.C.; Kirk, K.L., Meinwald, J. J. Am. Chem. Soc., 1966, 88, 108.
64. 43. Kobayashi, J.; Cheng, J.; Ishibashi, M.; Wälchli, M.R.; Yamamura, S.; Ohizumi, Y. J. Chem. Soc. Perkin Trans I, 1991, 1135-1137.
65. 44. Alvi, K.A.; Jaspars, M.; Crews, P.; Strulovici, B.; Oto, E. Bioorg. Med Chem. Lett. 1994, 4, 2447-2450.
66. 45. Kobayashi, J.; Tsuda, M.; Cheng, J.-F.; Ishibashi, M.; Takihawa, H.; Mori, K. Tetrahedron Lett. 1996, 37, 6775-6776.