A Simple and Highly Diastereoselective One-Pot Synthesis of 1,3-Diamines

Synlett

Volumn 1997, Issue 2, 1997, Pages 177-178

  Merla, Beatrix ^a   Arend, Michael ^a   Risch, Nikolaus ^a  

^a UNIVERSITY OF PADERBORN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542632174     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-729     Document Type: Article

References (28)

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15. Risch, N.; Arend, M. Angew. Chem. 1994, 106, 2531; Angew. Chem. Int. Ed. Engl. 1994, 33, 2422.
16. For an excellent review concerning the reduction of C=N double bonds by metal hydrides see: Hutchins, R. O; Hutchins, M. K. In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 25.
17. 2 / MeOH). The last fraction eluted was the 1,3-diamine 4.
18. 13C NMR, and mass spectra. Satisfactory microanalyses are obtained for all new compounds (C ±0.25, H ±0.19, N ±0.19).
19. Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412.
20. arom).
21. Preparation of the iminium salts 1: (a) Risch, N.; Arend, M. In Hauben-Weyl, 4th ed., Vol. E21b; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.: Thieme: Stuttgart, 1995; p 1925. (b) Opitz, G.; Hellmann, H.; Schubert, H. W. Liebigs Ann. Chem. 1959, 623, 117. Preparation of the enamines 2: (c) Carlson, R.; Nilsson, Å. Acta Chim Scand. B 1984, 38, 49. (d) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
22. Preparation of the iminium salts 1: (a) Risch, N.; Arend, M. In Hauben-Weyl, 4th ed., Vol. E21b; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.: Thieme: Stuttgart, 1995; p 1925. (b) Opitz, G.; Hellmann, H.; Schubert, H. W. Liebigs Ann. Chem. 1959, 623, 117. Preparation of the enamines 2: (c) Carlson, R.; Nilsson, Å. Acta Chim Scand. B 1984, 38, 49. (d) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
23. Preparation of the iminium salts 1: (a) Risch, N.; Arend, M. In Hauben-Weyl, 4th ed., Vol. E21b; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.: Thieme: Stuttgart, 1995; p 1925. (b) Opitz, G.; Hellmann, H.; Schubert, H. W. Liebigs Ann. Chem. 1959, 623, 117. Preparation of the enamines 2: (c) Carlson, R.; Nilsson, Å. Acta Chim Scand. B 1984, 38, 49. (d) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
24. Preparation of the iminium salts 1: (a) Risch, N.; Arend, M. In Hauben-Weyl, 4th ed., Vol. E21b; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.: Thieme: Stuttgart, 1995; p 1925. (b) Opitz, G.; Hellmann, H.; Schubert, H. W. Liebigs Ann. Chem. 1959, 623, 117. Preparation of the enamines 2: (c) Carlson, R.; Nilsson, Å. Acta Chim Scand. B 1984, 38, 49. (d) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
25. 5a: yield 65 %; Sb: yield 62 %. We tentatively assigned structure 5 to the 1,3-diamines derived from imines in analogy to the 1,3-diamines 4 derived from enamines 2.
26. Arend, M.; Risch, N. Angew. Chem. 1995, 107, 2861; Angew. Chem. Int. Ed. Engl. 1995, 34, 2639.
27. Arend, M.; Risch, N. Angew. Chem. 1995, 107, 2861; Angew. Chem. Int. Ed. Engl. 1995, 34, 2639.
28. d' Angelo, J.; Desmaële. D.; Dumas, F.; Guingant, A. Tetrahedron Asymmetry 1992, 3, 459.