O-tert-butyl-N-(chloromethyl)-N-methyl carbamate as a source of the MeNHCH2- synthon

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5597-5600

  Guijarro, Albert ^a   Ortiz, Javier ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; CYCLOPENTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605835     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01134-3     Document Type: Article

References (42)

1. 1. Seebach, D. Angew. Chem. Int. Ed. Engl. 1979, 18, 239-258.
2. 2. See, for instance: (a) Meyers, A. I.; Hellring, S.; Hoeve, W. T. Tetrahedron Lett. 1981, 22, 5115-5118.
3. (b) Duhamel, L.; Duhamel, P.; Fonquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J.-C.; Ravard, A.; Soliard, R.; Valnot, J.-Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506.
4. (c) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 776, 3231-3239.
5. (d) Choy, J. M.; Park, S. B. J. Org. Chem. 1992, 57, 2220-2222.
6. 3. For reviews, see: (a) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Ber. 1984, 84, 471-523.
7. (b) Saavedra, J. E. In Umpoled Synthons, Hase, T. A. Ed.; John Wiley & Sons: New York, 1987; pp. 107-121.
8. 4. For leading references, see: (a) Lohman, J.-J.; Seebach, D.; Syfrig, M. A.; Yoshifuji, M. Angew. Chem. Int. Ed. Engl. 1981, 20, 128-129.
9. (b) Seebach, D.; Yoshifuji, M. Helv. Chim. Acta 1981, 64, 643-647.
10. (c) Wykypiel, W..; Lohmann, J.-J.; Seebach, D. Helv. Chim. Acta 1981, 64, 1337-1346.
11. (d) Seebach, D.; Lohmann, J.-J.; Syfrig, M. A.; Yoshifuji, M. Tetrahedron 1983, 39, 1963-1974.
12. (e) Seebach, D.; Huber, I. M. P.; Syfrig, M. A. Helv. Chim. Acta 1987, 70, 1357-1379.
13. (f) Meyers, A. I.; Gottlieb, L. J. Org. Chem. 1990, 55, 5659-5662.
14. (h) Meyers, A. I.; Shave, T. T. J. Org. Chem. 1991, 56, 2751-2755.
15. (i) Meyers, A. I.; Milot, G. J. Org. Chem. 1993, 58, 6538-6540.
16. (j) Guiles, J. W.; Meyers, A. I. J. Org. Chem. 1991, 56, 6873-6878.
17. (k) Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197-1200.
18. (l) Beaak, P.; Lee, W.-K. J. Org. Chem. 1990, 55, 2278-2580.
19. (m) Beak, P.; Yum, E. K. J. Org. Chem. 1993, 58, 823-824.
20. (n) Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 823-824.
21. (o) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231-3239.
22. (p) Sanner, M. A. Tetrahedron Lett. 1989, 30, 1909-1912.
23. (q) Williams, R. M.; Kwast, E. Tetrahedron Lett. 1989, 30, 451-454.
24. (r) Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757-3758.
25. 5. For leading references, see: (a) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495-498.
26. (b) Pearson, W. H.; Szurd, D. P.; Harter, W. G. Tetrahedron Lett. 1988, 29, 761-764.
27. (d) Pearson, W. H.; Lindbeck, A. C. J. Org. Chem. 1989, 54, 5651-5654.
28. (d) Peaarson, W. H.; Lindbeck, A. C. J. Am. Chem. Soc. 1991, 113, 8546-8548.
29. (e) Burchat, A. F.; Chong, J. M.; Park, S. B. Tetrahedron Lett. 1993, 34, 51-54.
30. (f) Pearson, W. H.; Lindbeck, A. C.; Kampf, J. W. J. Am. Chem. Soc. 1993, 115, 2622-2632.
31. (g) Gawley, R. E.; Zhang, Q. J. Am. Chem. Soc. 1993, 115, 7515-7516.
32. (h) See also ref 2d.
33. 6. Tsunoda, T.; Fujiwara, K.; Yamamoto, Y.; Ito, S. Tetrahedron Lett. 1991, 32, 1975-1978.
34. 7. For a monography, see: Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988.
35. 8. (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400.
36. (b) For a review, see: Yus, M. Chem. Soc. Rev., submitted.
37. 9. For a review on functionalised organolithium compounds, see: Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
38. 10. For a monography on the Barbier reaction, see: Blomberg, C. The Barbier Reaction and Related One-Pot Processes; Springer-Verlag: Berlin, 1993.
39. 11. For the last paper from our laboratory on an arene-catalysed reaction, see: Almena, J.; Foubelo, F.; Yus, M. J. Org. Chem. 1996, 61, 1859-1862.
40. 12. Prepared following the literature procedure in 98% yield: Smith, M. B.; Dembofsky, B. T.; Son, Y. C. J. Org. Chem. 1994, 59, 1719-1725.
41. f = 0.75 (silica gel, pentane/ethyl acetate: 1/4).
42. 14 In other examples for the transformation 2→3 carried out in our laboratory we obtained yields better than 90%.