Nitriles under palladium-catalyzed hydrogenation conditions as substitutes for aldehydes in the reaction with 1,2-amino alcohols: Formation of 1,3-oxazolidines and reductive N-alkylation

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7187-7190

  Hénin, Françoise ^a   Létinois, Stéphane ^a   Muzart, Jacques ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030699461     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01728-0     Document Type: Article

References (29)

1. Hénin, F.; Muzart, J. Tetrahedron: Asymmetry 1992, 3, 1161-1164; Muzart, J.; Hénin, F.; Jamal Aboulhoda, S. Tetrahedron: Asymmetry 1997, 8, 381-389.
2. Hénin, F.; Muzart, J. Tetrahedron: Asymmetry 1992, 3, 1161-1164; Muzart, J.; Hénin, F.; Jamal Aboulhoda, S. Tetrahedron: Asymmetry 1997, 8, 381-389.
3. Thorey, C.; Hénin, F.; Muzart, J. Tetrahedron: Asymmetry 1996, 7, 975-976.
4. Beckett, A.H.; Jones, G.R. Tetrahedron 1977, 33, 3313-3316.
5. Bergmann, E.D. Chem. Rev. 1953, 53, 309-352.
6. For recent references, see: Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835-875; Kumar, G.B.; Patel, H.V.; Shah, A.C.; Trenkle, M.; Cardin, C.J. Tetrahedron: Asymmetry 1996, 7, 3391-3396; O'Brien, P.; Warren, S. Tetrahedron: Asymmetry 1996, 7, 3431-3444; Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002. Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226; Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Gutiérrez-Rodriguez, A. Tetrahedron Lett. 1996, 37, 10761-10770; Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627-3630. Koskinen, A.M.P.; Otsomaa, L.A. Tetrahedron 1997, 53, 6473-6484.
7. For recent references, see: Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835-875; Kumar, G.B.; Patel, H.V.; Shah, A.C.; Trenkle, M.; Cardin, C.J. Tetrahedron: Asymmetry 1996, 7, 3391-3396; O'Brien, P.; Warren, S. Tetrahedron: Asymmetry 1996, 7, 3431-3444; Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002. Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226; Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Gutiérrez-Rodriguez, A. Tetrahedron Lett. 1996, 37, 10761-10770; Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627-3630. Koskinen, A.M.P.; Otsomaa, L.A. Tetrahedron 1997, 53, 6473-6484.
8. For recent references, see: Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835-875; Kumar, G.B.; Patel, H.V.; Shah, A.C.; Trenkle, M.; Cardin, C.J. Tetrahedron: Asymmetry 1996, 7, 3391-3396; O'Brien, P.; Warren, S. Tetrahedron: Asymmetry 1996, 7, 3431-3444; Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002. Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226; Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Gutiérrez-Rodriguez, A. Tetrahedron Lett. 1996, 37, 10761-10770; Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627-3630. Koskinen, A.M.P.; Otsomaa, L.A. Tetrahedron 1997, 53, 6473-6484.
9. For recent references, see: Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835-875; Kumar, G.B.; Patel, H.V.; Shah, A.C.; Trenkle, M.; Cardin, C.J. Tetrahedron: Asymmetry 1996, 7, 3391-3396; O'Brien, P.; Warren, S. Tetrahedron: Asymmetry 1996, 7, 3431-3444; Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002. Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226; Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Gutiérrez-Rodriguez, A. Tetrahedron Lett. 1996, 37, 10761-10770; Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627-3630. Koskinen, A.M.P.; Otsomaa, L.A. Tetrahedron 1997, 53, 6473-6484.
10. For recent references, see: Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835-875; Kumar, G.B.; Patel, H.V.; Shah, A.C.; Trenkle, M.; Cardin, C.J. Tetrahedron: Asymmetry 1996, 7, 3391-3396; O'Brien, P.; Warren, S. Tetrahedron: Asymmetry 1996, 7, 3431-3444; Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002. Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226; Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Gutiérrez-Rodriguez, A. Tetrahedron Lett. 1996, 37, 10761-10770; Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627-3630. Koskinen, A.M.P.; Otsomaa, L.A. Tetrahedron 1997, 53, 6473-6484.
11. For recent references, see: Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835-875; Kumar, G.B.; Patel, H.V.; Shah, A.C.; Trenkle, M.; Cardin, C.J. Tetrahedron: Asymmetry 1996, 7, 3391-3396; O'Brien, P.; Warren, S. Tetrahedron: Asymmetry 1996, 7, 3431-3444; Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002. Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226; Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Gutiérrez-Rodriguez, A. Tetrahedron Lett. 1996, 37, 10761-10770; Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627-3630. Koskinen, A.M.P.; Otsomaa, L.A. Tetrahedron 1997, 53, 6473-6484.
12. For recent references, see: Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835-875; Kumar, G.B.; Patel, H.V.; Shah, A.C.; Trenkle, M.; Cardin, C.J. Tetrahedron: Asymmetry 1996, 7, 3391-3396; O'Brien, P.; Warren, S. Tetrahedron: Asymmetry 1996, 7, 3431-3444; Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002. Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226; Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Gutiérrez-Rodriguez, A. Tetrahedron Lett. 1996, 37, 10761-10770; Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627-3630. Koskinen, A.M.P.; Otsomaa, L.A. Tetrahedron 1997, 53, 6473-6484.
13. For recent references, see: Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835-875; Kumar, G.B.; Patel, H.V.; Shah, A.C.; Trenkle, M.; Cardin, C.J. Tetrahedron: Asymmetry 1996, 7, 3391-3396; O'Brien, P.; Warren, S. Tetrahedron: Asymmetry 1996, 7, 3431-3444; Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001-4002. Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226; Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Gutiérrez-Rodriguez, A. Tetrahedron Lett. 1996, 37, 10761-10770; Allin, S.M.; Northfield, C.J.; Page, M.I.; Slawin, A.M.Z. Tetrahedron Lett. 1997, 38, 3627-3630. Koskinen, A.M.P.; Otsomaa, L.A. Tetrahedron 1997, 53, 6473-6484.
14. 2/g and contains 50% of water. The carbon type of this catalyst is activated wood (Technical information from Engelhard Company).
15. An almost diastereomerically pure form of 2a was obtained. The cis-relative configuration at C-2 was deduced from literature data: Agami, C.; Rizk, T. Tetrahedron 1985, 41, 537-540 and ref. therein.
16. Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Recueil 1997, 1101-1113.
17. 1H NMR signals corresponding to the hydrogen gem to the phenyl group (doublet for each compound).
18. 4; Engelhardt, T.; Crossley, F.S.; Sprague, J.M. J. Am. Chem. Soc. 1950, 72, 2718-2722; Eleved, M.B.; Hogeven, H.; Schudde, E.P. J. Org. Chem. 1986, 51, 3635-3642; Polyak, F.; Dorofeeva, T.; Zelchan, G. Synth. Commun. 1995, 25, 2895-2900.
19. 4; Engelhardt, T.; Crossley, F.S.; Sprague, J.M. J. Am. Chem. Soc. 1950, 72, 2718-2722; Eleved, M.B.; Hogeven, H.; Schudde, E.P. J. Org. Chem. 1986, 51, 3635-3642; Polyak, F.; Dorofeeva, T.; Zelchan, G. Synth. Commun. 1995, 25, 2895-2900.
20. 4; Engelhardt, T.; Crossley, F.S.; Sprague, J.M. J. Am. Chem. Soc. 1950, 72, 2718-2722; Eleved, M.B.; Hogeven, H.; Schudde, E.P. J. Org. Chem. 1986, 51, 3635-3642; Polyak, F.; Dorofeeva, T.; Zelchan, G. Synth. Commun. 1995, 25, 2895-2900.
21. 5, m).
22. For a highlight definition of the domino reactions, see: Tietze, L.F. Chem. Rev. 1996, 96, 115-136.
23. See also: Cottineau, F.; Maigrot, N.; Mazaleyrat, J.P. Tetrahedron Lett. 1985, 26, 421-424. Bradshaw, J.S.; Krakowiak, K.E.; Izatt, R.M. Tetrahedron Lett. 1989, 30, 803-806. De Souza, S.E.; O'Brien, P. Tetrahedron Lett. 1997, 38, 4885-4888.
24. See also: Cottineau, F.; Maigrot, N.; Mazaleyrat, J.P. Tetrahedron Lett. 1985, 26, 421-424. Bradshaw, J.S.; Krakowiak, K.E.; Izatt, R.M. Tetrahedron Lett. 1989, 30, 803-806. De Souza, S.E.; O'Brien, P. Tetrahedron Lett. 1997, 38, 4885-4888.
25. See also: Cottineau, F.; Maigrot, N.; Mazaleyrat, J.P. Tetrahedron Lett. 1985, 26, 421-424. Bradshaw, J.S.; Krakowiak, K.E.; Izatt, R.M. Tetrahedron Lett. 1989, 30, 803-806. De Souza, S.E.; O'Brien, P. Tetrahedron Lett. 1997, 38, 4885-4888.
26. Tanaka, K.; Ushio, H.; Kawabata, Y.; Suzuki, H. J. Chem. Soc., Perkin Trans I 1991, 1445-1452.
27. Saavedra, J.E. J. Org. Chem. 1985, 50, 2271-2273.
28. 5, m).
29. The relative low isolated yield of 3e came from lost of material due to some difficulties in the course of the purification.