One-pot synthesis of protected homoallyl amines

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 997-1000

  Veenstra, Siem J ^a   Schmid, Priska ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562059     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02458-6     Document Type: Article

References (49)

1. 1. Review: Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Schreiber, S.L., Ed.; Pergamon Press; Oxford, 1991, pp. 1047-1082.
2. 2. Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
3. (b) Kleinman, E.F.; Volkmann, R.A. In Comprehensive Organic Synthesis, Vol. 2; Trost, B.M.; Fleming, I.; Heathcock, C.H., Eds.; Pergamon Press; Oxford, 1991, pp. 975-1006.
4. (c) Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243.
5. (d) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1.
6. 3. (a) Wang, J.; Zhou, J.; Zhang, Y. Synth. Commun. 1996, 26, 3395.
7. (b) Wang, J.; Zhang, Y.; Bao, W. Synth. Commun. 1996, 26, 2473.
8. (c) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187.
9. (d) Kumaraswamy, S.; Nagabrahmanandachari, S.; Kumara Swamy, K.C. Synth. Commun. 1996, 26, 729.
10. (e) Yanagisawa, A.; Ogasawara, K.; Yasue, K.; Yamamoto, H. J. Chem. Soc. Chem. Commun. 1996, 367.
11. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649.
12. (g) Bellucci C.; Cozzi, P.G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289.
13. (h) Bossard, F.; Dambrin, V.; Lintanf, V.; Beuchet, P.; Mosset, P. Tetrahedron Lett. 1995, 36, 6055.
14. (i) Beuchet, P.; Le Marrec, N.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
15. (j) Wuts, P.G.M.; Jung, Y.-W. J. Org. Chem. 1991, 56, 365.
16. Enantioselective methods: (k) Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136.
17. (l) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
18. (m) Enders, D.; Schankat, J.; Klatt, M. Synlett. 1994, 795.
19. 4. (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561.
20. (b) Hoffman, R.V.; Nayyar, N.K.; Shankweiler, J.M.; Klinekole III, B.W. Tetrahedron Lett. 1994, 35, 3231.
21. (c) Katritzky, A.R.; Shobana, N.; Harris, P.A. Organometallics 1992, 11, 1381.
22. (d) Roos, E.C.; Hiemstra, H.; Speckamp, W.N.; Kaptein, B.; Kamphuis, J.; Schoemaker, H.E. Recl. Trav. Chim. Pays-Bas 1992, 111, 360.
23. (e) Naota, T.; Nakato, T.; Murahashi, S.-I. Tetrahedron Lett. 1990, 31, 7475.
24. (f) Bernardi, A,; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949.
25. (g) Earle, M.J.; Fairhurst, R.A.; Heaney, H.; Papageorgiou, G. Synlett. 1990, 621.
26. (h) Mooiweer, H.H.; Hiemstra, H.; Speckamp, W.N. Tetrahedron 1989, 45, 4627.
27. 5. (a) Ofner, S.; Hauser, K.; Schilling, W.; Vassout, A.; Veenstra, S.J. Bioorg. Med. Chem. Lett. 1996, 6, 1623.
28. (b) Veenstra, S.J.; Hauser, K.; Schilling, W.; Betschart, C.; Ofner, S. Bioorg. Med. Chem. Lett. submitted.
29. (c) Schilling, W.; Ofner, S.; Veenstra, S. J. Europ. Pat. EP 532456 (1990).
30. 4. After evaporation of the solvents under reduced pressure the crude product was purified by distillation or chromatography on silica gel (hexane/ethyl acetate as eluent).
31. 7. Schmid, C.R.; Bradley, D.A. Synthesis 1992, 587.
32. 8. Stereochemistry not determined.
33. 9. Compound 12 was prepared in analogy to a published procedure: Hey, D.H.; Williams, J.M. J. Chem. Soc. 1950, 1682.
34. 10. Paquin, A. Angew. Chem. 1948, 60, 318.
35. 3. The mixture was filtered and the crystalline product was washed with water and diethyl ether. Recrystallization of the crude product from isopropanol gave 39 in 76% yield. Mp. 170-172°C.
36. 12. Acylimines, being in general unstable species, are isolable when stabilizing substituents are present. See for instance: (a) Vidal, J., Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791.
37. (b) Dobrev, A.; Benin, V.; Nechev, L. Liebigs Ann. Chem. 1992, 863.
38. (c) Malassa, I.; Matthies, D. Chemiker Zeitung 1987, 111, 181.
39. (d) Kupfer, R.; Meier, S.; Wuerthwein, E.-U. Synthesis 1984, 688.
40. In the course of our studies a paper appeared where acylimines, generated in situ from aldehydes or acetals and a carbamate, were condensed with substituted crotylsilanes: Panek, J.S.; Jain, N.F. J. Org. Chem. 1994, 59, 2674.
41. 13. (a) Krow, G.R.; Henz, K.J.; Szczepanski, S.W. J. Org. Chem. 1985, 50, 1888.
42. (b) Harter, H.P.; Liisberg, S. Acta Chem. Scand. 1968, 22, 2685.
43. (c) Cava, M.P.; Wilkins, Jr., C.K.; Dalton, D.R.; Bessho, K. J. Org. Chem. 1965, 30, 3772.
44. 14. (a) Review: Zaugg, H.E., Martin, W.B. In Organic Reactions, Vol. 14; Adams, R.; Blatt, A.H.; Boekelheide, V.; Cairns, T.L. Cope; A.C.; Niemann, C., Eds.; John Wiley & Sons, Inc., New York, 1965, pp. 52-266.
45. (b) Kodama, Y.; Okamura, M.; Yanabu, N.; Taguchi, T. Tetrahedron Lett. 1996, 37, 1061.
46. (c) Tohyama, Y.; Tanino, K.; Kuwajima, I. J. Org. Chem. 1994, 59, 518.
47. (d) Krow, G.R.; Pannella, H; Figures, W. J. Chem. Engineering Data 1972, 17, 116.
48. (e) Merten, R.; Mueller, G. Angew. Chem. 1962, 74, 866.
49. 15. The reaction is slightly exothermic and a precipitate which often forms during the reaction can cause stirring problems. On large scale it is advisable to change the mode of addition by simultaneously adding a methylene chloride solution of aldehyde, carbamate and allyltrimethylsilane and a methylene chloride solution of borontrifluoride etherate to the well stirred and cooled reaction mixture.