An azetidinium ion approach to 3-aryloxy-3-aryl-1-propanamines

Tetrahedron Letters

Volumn 43, Issue 41, 2002, Pages 7333-7335

  O'Brien, Peter ^a   Phillips, David W ^a   Towers, Timothy D ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

3 aryloxy 3 aryl 1 propanamines; Amino alcohols; Azetidinium ions; Neighbouring group effects; Phenols

Indexed keywords

AMINE; AZETIDINE; CHLORIDE; ION; PHENOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE DEPENDENCE;

EID: 0037037886     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01724-0     Document Type: Article

References (25)

1. Wong D.T., Robertson D.W., Bymaster F.P., Krushinski J.H., Reid L.R. Life Sciences. 43:1988;2049.
2. Chovinard G.A. J. Clin. Psychiatry. 46:1985;32.
3. Devine P.N., Heid R.M., Tschaen D.M. Tetrahedron. 53:1997;6739.
4. Ratz A.M., Weigel L.O. Tetrahedron Lett. 40:1999;2239.
5. Ohkuma T., Ishii D., Takeno H., Noyori R. J. Am. Chem. Soc. 122:2000;6510.
6. Miles W.H., Fialcowitz E.J., Halstead E.S. Tetrahedron. 57:2001;9925.
7. de Sousa S.E., O'Brien P., Poumellec P. J. Chem. Soc., Perkin Trans. 1. 1998;1483.
8. Cuthbertson E., O'Brien P., Towers T.D. Synthesis. 2001;693.
9. O'Brien P., Towers T.D. J. Org. Chem. 67:2002;304.
10. For recent examples and leading references, see: (a) Lowden, C. T.; Mendoza, J. S. Tetrahedron Lett. 2002, 43, 979; (b) Graham, M. A.; Wadsworth, A. H.; Thornton-Pett, M.; Rayner, C. M. Chem. Commun. 2001, 966; (c) Nagle, A. S.; Salvatore, R. N.; Chong, B.-D.; Jung, K. W. Tetrahedron Lett. 2000, 41, 3011; (d) Chuang, T.-H.; Sharpless, K. B. Org. Lett. 1999, 1, 1435.
11. For recent examples and leading references, see: (a) Lowden, C. T.; Mendoza, J. S. Tetrahedron Lett. 2002, 43, 979; (b) Graham, M. A.; Wadsworth, A. H.; Thornton-Pett, M.; Rayner, C. M. Chem. Commun. 2001, 966; (c) Nagle, A. S.; Salvatore, R. N.; Chong, B.-D.; Jung, K. W. Tetrahedron Lett. 2000, 41, 3011; (d) Chuang, T.-H.; Sharpless, K. B. Org. Lett. 1999, 1, 1435.
12. For recent examples and leading references, see: (a) Lowden, C. T.; Mendoza, J. S. Tetrahedron Lett. 2002, 43, 979; (b) Graham, M. A.; Wadsworth, A. H.; Thornton-Pett, M.; Rayner, C. M. Chem. Commun. 2001, 966; (c) Nagle, A. S.; Salvatore, R. N.; Chong, B.-D.; Jung, K. W. Tetrahedron Lett. 2000, 41, 3011; (d) Chuang, T.-H.; Sharpless, K. B. Org. Lett. 1999, 1, 1435.
13. For recent examples and leading references, see: (a) Lowden, C. T.; Mendoza, J. S. Tetrahedron Lett. 2002, 43, 979; (b) Graham, M. A.; Wadsworth, A. H.; Thornton-Pett, M.; Rayner, C. M. Chem. Commun. 2001, 966; (c) Nagle, A. S.; Salvatore, R. N.; Chong, B.-D.; Jung, K. W. Tetrahedron Lett. 2000, 41, 3011; (d) Chuang, T.-H.; Sharpless, K. B. Org. Lett. 1999, 1, 1435.
14. Gaertner V.R. J. Org. Chem. 33:1968;523.
15. Beaulieu P.L., Wernic D. J. Org. Chem. 61:1996;3635.
16. Bakalarz-Jeziorna A., Helinski J., Krawiecka B., Michalski J., Portzebowski M.J. Tetrahedron. 55:1999;12211.
17. Concellon J.M., Bernad P.L., Pérez-Andrés J.A. Tetrahedron Lett. 41:2000;1231.
18. Bakalarz-Jeziorna A., Helinski J., Krawiecka B. J. Chem. Soc., Perkin Trans. 1. 2001;1086.
19. Kane M.P., Szumuszovicz J. J. Org. Chem. 46:1981;3728.
20. Coffey D.S., McDonald A.I., Overman L.E. J. Org. Chem. 64:1999;8741.
21. Amino alcohol 3 was obtained by sodium borohydride reduction of the corresponding amino ketone according to the procedure described in Ref. 4.
22. 21NO requires M+H, 256.1701.
23. Amino alcohol 5 was synthesised via a two-step sequence: (i) conjugate addition of lithium dimethylamide to ethyl cinnamate furnished the N,N-dimethylamino ester in 33% yield; (ii) lithium aluminium hydride reduction of the ester then gave amino alcohol 5 in quantitative crude yield. For a representative procedure for the conjugate addition step, see: O'Brien, P.; Porter, D. W.; Smith, N. M. Synlett 2000, 1336.
24. 1H NMR spectroscopy in the presence of the chiral shift reagent (R)-2,2,2-trifluoro-1-(9-anthryl)ethanol.
25. 3).