Synthesis of syn- and anti-1,2-amino alcohols by regioselective ring opening reactions of cis-3-aminooxetanes

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3707-3710

  Bach, Thorsten ^a   Schröder, Jürgen ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; PSEUDOEPHEDRINE;

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

EID: 0343144854     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00721-1     Document Type: Article

References (34)

1. Bach, T. Angew. Chem. 1996, 108, 976-977; Angew. Chem. Int. Ed. Engl. 1996, 35, 884-886.
2. Bach, T. Angew. Chem. 1996, 108, 976-977; Angew. Chem. Int. Ed. Engl. 1996, 35, 884-886.
3. Recent reviews about the Paternò-Büchi reaction: (a) Mattay, J.; Conrads, R.; Hoffmann, R. in Methoden der Organischen Chemie (Houben-Weyl) 4te Aufl. (eds.: Helmchen, G., Hoffmann, R. W.; Mulzer, J.; Schaumann, E.), Thieme, Stuttgart, 1995, Band E 21c, 3133-3178.
4. (b) Porco, J. A., Schreiber, S. L. in Comprehensive Organic Synthesis (ed.: Trost, B.), Pergamon Press, Oxford, 1991, vol. 5, 151-192.
5. (c) Carless, H. A. J. in Synthetic Organic Photochemistry (ed.: Horspool, W. M.), Plenum Press, New York, 1984, 425-487.
6. (d) Jones II, G. in Organic Photochemistry (ed.: Padwa, A.), Dekker, New York, 1981, vol. 5, 1-123.
7. Reviews: (a) Gante, J. Angew. Chem. 1994, 106, 1780-1802; Angew. Chem. Int. Ed. Engl. 1994, 34, 1699-1720.
8. Reviews: (a) Gante, J. Angew. Chem. 1994, 106, 1780-1802; Angew. Chem. Int. Ed. Engl. 1994, 34, 1699-1720.
9. (b) Weidmann, B. Chimia 1991, 45, 367-376.
10. (c) Huff, J. R. J. Med. Chem. 1991, 34, 2305-2314.
11. (d) Reetz, M. T. Angew. Chem. 1991, 103, 1554-1573; Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1546.
12. (d) Reetz, M. T. Angew. Chem. 1991, 103, 1554-1573; Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1546.
13. A related method for the ring opening of 3-oxetanols has been described: Bach, T.; Kather, K. J. Org. Chem. 1996, 61, 3900-3901.
14. (a) Bach, T.; Kather, K. J. Org. Chem. 1996, 61, 7642-7643.
15. (b) Xianming, H.; Kellogg, R. M. Tetrahedron: Asymmetry, 1995, 6, 1399-1408.
16. (c) Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett., 1994, 35, 7089-7092.
17. (d) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett., 1994, 35, 761-764.
18. (e) Amouroux, R.; Jatczak, M.; Chastrette, M. Bull. Soc. Chim. Fr., 1987, 505-510.
19. (f) Yamaguchi, M.; Nobayashi, Y.; Hirao, I. Tetrahedron, 1984, 40, 4261-4266.
20. (g) Eis, M. J.; Wrobel, J. E.; Ganem, B. J. Am. Chem. Soc., 1984, 106, 3693-3694.
21. (h) Firgo, H. A.; Weber, W. P. J. Organomet. Chem., 1981, 222, 201-209.
22. (i) Krishnamurthy, S.; Brown, H. C. J. Org. Chem., 1979, 44, 3678-3682.
23. For other methods to obtain alternatively either syn-or anti-1,2-amino alcohols by C-C bond formation, see Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677-2685.
24. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991, 327-330.
25. 3, 75.5 MHz, 303 K): δ = 20.2 (q), 44.3 (t), 61.8 (t), 65.7 (d), 84.4 (d), 126.9 (d), 127.0 (d), 127.0 (d), 127.4 (d), 128.1 (d), 128.4 (d), 135.5 (s), 139.1 (s), 158.8 (s).
26. a of ca. -2.5 has been reported, see Searles, S. in Comprehensive Heterocyclic Chemistry (ed.: Katritzky, A. R.), Pergamon Press, Oxford, 1984, vol. 7, p. 363-402.
27. The exo-ring opening of epoxides via an intramolecular oxygen nucleophile is well precedented. For some selected examples, see (a) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1108-1110.
28. (b) Roush, W. R.; Straub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127.
29. (c) Paterson, I.; Boddy, I.; Mason, I. Tetrahedron Lett. 1987, 28, 5205-5208.
30. (d) Romeo, S.; Rich, D. H. Tetrahedron Lett. 1994, 35, 4939-4942.
31. Intramolecular ring opening reaction of oxetanes by oxygen nucleophiles catalyzed by acids or Lewis acids: (a) Corey, E. J., Raju, N. Tetrahedron Lett. 1984, 25, 4549-4552.
32. (b) Khan, N.; Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Perkin Trans. I 1991, 865-870.
33. (c) Itoh, A.; Hirose, Y.; Kashiwagi, H.; Masaki, Y. Heterocycles 1994, 38, 2165-2169.
34. Hutchins, R. O.; Kandasamy, D.; Dux III, F.; Maryanoff, C. A.; Rotstein, D.; Goldsmith, B.; Burgoyne, W.; Cistone, F.; Dalessandro, J.; Puglis, J. J. Org. Chem. 1978, 43, 2259-2267.