Asymmetric synthesis of α-substituted β-amino sulfones by aza-Michael addition/α-alkylation

Synlett

Volumn , Issue 6, 1999, Pages 741-743

  Enders, Dieter ^a   Müller, Stephan F ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Alkenyl sulfones; Amines; Asymmetric synthesis; Michael addition; Sulfones; alkylation

Indexed keywords

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0344731334     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-972952     Document Type: Article

References (34)

1. a) Simpkins, N. S. In Sulphones in Organic Synthesis, Tetrahedron Organic Chemistry Series, Vol. 10; Baldwin, J. E.; Magnus, P. D., Eds; Pergamon: Oxford, 1993.
2. b) Patai, S.; Rappoport, Z.; Stirling, C. J. The Chemistry of Functional Groups: The Chemistry of Sulphones and Sulphoxides; Wiley: Chichester, 1988.
3. c) Schank, K. In Houben-Weyl, 4th ed., Vol. E11/2, p 1132.
4. d) Durst T. In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R.; Ollis, W. D, Eds.; Pergamon: Oxford, 1979, p 171.
5. e) Simpkins, N. S. Tetrahedron 1990, 46, 6951.
6. a) Tanikaga, R.; Shibata, N.; Yoneda, T. J. Chem. Soc., Perkin Trans. 1 1997, 2253.
7. b) Campbell, R. V. M.; Crombie, L.; Findley, D. A. R.; King, R. W.; Pattenden, G.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1975, 897.
8. For some recent examples see: a) Knight, D. W.; Sibley, A. W. J. Chem. Soc., Perkin Trans. 1 1997, 2179.
9. b) Hart, D. J.; Li, J.; Wu, W.-L.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023.
10. c) Magnus, N.; Magnus, P. Tetrahedron Lett. 1997, 38, 3491.
11. d) Solladié-Cavallo, A.; Roche, D.; Fischer, J.; De Cian, A. J. Org. Chem. 1996, 61, 2690.
12. e) Markó, I. E.; Murphy, F.; Dolan, S. Tetrahedron Lett. 1996, 37, 2089.
13. Recent examples: a) Tanimoto, H.; Oritani, T. Tetrahedron 1997, 53, 3527.
14. b) Alonso, D. A.; Falvello, L. R.; Mancheno, B.; Nájera, C.; Tomás, M. J. Org. Chem. 1996, 61, 5004.
15. c) Bonete, P.; Nájera, C. Tetrahedron 1996, 52, 4111.
16. d) Houston, T. A.; Koreeda, M. Synth. Commun. 1994, 24, 393.
17. e) Pine, S. H.; Shen, G.; Bautista, J.; Sutton, Jr., C.; Yamada, W.; Apodaca, L. J. Org. Chem. 1990, 55, 2234.
18. f) Isobe, M.; Obeyama, J.; Funabashi, Y.; Goto, T. Tetrahedron Lett. 1988, 29, 4773.
19. g) Larcheveque, M.; Sanner, C. Tetrahedron 1988, 44, 6407.
20. h) Eisch, J. J.; Behrooz, M.; Dua, S. K. J. Organomet. Chem. 1985, 121.
21. i) Eisch, J. J.; Galle, J. E. J. Org. Chem. 1980, 45, 4534.
22. a) Sasaki, N. A.; Dockner, M.; Chiaroni, A.; Riche, C.; Potier, P. J. Org. Chem. 1997, 62, 765 and references cited therein.
23. b) Alonso, D. A.; Costa, A.; Mancheno, B.; Nájera, C. Tetrahedron 1997, 53, 4791.
24. Enders, D.; Müller,S.F.; Raabe, G. Angew. Chem. 1999, 111, 212; Angew. Chem., Int. Ed. Engl. 1999, 38, 195.
25. Enders, D.; Müller,S.F.; Raabe, G. Angew. Chem. 1999, 111, 212; Angew. Chem., Int. Ed. Engl. 1999, 38, 195.
26. a) Enders, D, in A symmetric Synthesis, Vol. 3; Morrison, J. D., Ed.; Academic: Orlando, 1984, p 275.
27. b) Enders, D.; Fey, P.; Kipphardt, H. Org. Synth. 1987, 65, 173; 183.
28. Enders, D.; Lochtman, R.; Meiers, M.; Müller, S. F.; Lazny, R. Synlett 1998, 1182.
29. Yamazaki, N.; Kibayashi, C. J. Am. Chem. Soc. 1989, 111, 1396.
30. Crystallography data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 115145. Copies of the data can be obtained tree of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
31. b) Software for preparing the ball-and-stick plot representation: Ball & Stick Version 2.2, Falk, A.; Müller, N.; Schoppel, G.; Webb, L., Linz (Austria), Stafford (UK).
32. ortho→CHN.
33. 2S: C 73.67, H 7.17, N 3.44. Found: C 73.47, H 7.09, N 3.40.
34. All new compounds showed suitable spectroscopic data (IR, MS, NMR) and correct elemental analyses or high-resolution mass spectra.