Enantioselective synthesis of β-amino sulfones by aza-Michael addition to alkenyl sulfones

Angewandte Chemie - International Edition

Volumn 38, Issue 1-2, 1999, Pages 195-197

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

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Aminations; Asymmetric synthesis; Chiral auxiliaries; Michael additions; Sulfones

Indexed keywords

ALKENYL GROUP; SULFONE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NITROSATION; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0345390148     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990115)38:1/2<195::aid-anie195>3.0.co;2-6     Document Type: Article

References (46)

1. a) N. S. Simpkins in Sulphones in Organic Synthesis, Tetrahedron Organic Chemistry Series. Vol. 10 (Eds.: J. E. Baldwin, P. D. Magnus), Pergamon, Oxford, 1993;
2. b) The Chemistry of Functional Groups: The Chemistry of Sulphones and Sulphoxides, (Eds.: S. Patai, Z. Rappoport, C. J. Stirling), Wiley, Chichester, 1988;
3. c) K. Schank, Methoden Org. Chem. (Houben-Weyl) 4th ed 1985, Vol. E11/2, pp. 1132-1136;
4. d) T. Durst in Comprehensive Organic Chemistry, Vol. 3 (Eds.: D. H. R. Barton, W. D. Ollis), Pergamon, Oxford, 1979, pp. 171-213;
5. e) N. S. Simpkins, Tetrahedron 1990, 46, 6951-6984;
6. f) L. Field, Synthesis 1978, 713-740.
7. a) P. Perlmutter in Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series, Vol. 9 (Eds.: J. E. Baldwin, P. D. Magnus), Pergamon, Oxford, 1992;
8. b) M. Schäfer, K. Drauz, M. Schwarm, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1995, Vol. E21/5, pp. 5588-5642;
9. c) D. Enders, H. Wahl, W. Bettray, Angew. Chem. 1995, 107, 527-529; Angew. Chem. Int. Ed. Engl. 1995, 34, 453-457, and references therein.
10. c) D. Enders, H. Wahl, W. Bettray, Angew. Chem. 1995, 107, 527-529; Angew. Chem. Int. Ed. Engl. 1995, 34, 453-457, and references therein.
11. a) D. Braghiroli, R. Avallone, M. D. Di Bella, Tetrahedron: Asymmetry 1997, 8, 2209-2213:
12. b) H. Nakamura, H. Wu, J. Kobayashi, M. Kobayashi, Y. Ohizumi, Y. Hirata, J. Org. Chem. 1985, 50, 2494-2497;
13. c) Y. Ichikawa, Tetrahedron Lett. 1988, 21, 4957-4958;
14. d) B. Beagley, P. H. Crackett, R. G. Pritchard, R. J Stoodley, J. Chem. Soc. Perkin Trans. J 1990, 773-781;
15. e) Y. Girard, M. Larue, T. R. Jones, J. Rokach, Tetrahedron Lett. 1982, 23, 1023-1026.
16. R. Pauly, A. Sasaki, P. Portier, Tetrahedron Lett. 1994, 35, 237-240.
17. M. Hirama, H. Hioki, S. Ito, Tetrahedron Lett. 1988, 29, 3125-3128.
18. J. de Blas, J. C. Carretero, E. Dominguez. Tetrahedron Lett. 1994, 35, 4603-4606.
19. J. C. Wu, T. Pathak, W. Tong, J. M. Vial, G. Remaud, J. Chattopadhyaya, Tetrahedron 1988, 44, 6705-6722.
20. J. C. Carretero, R. G. Arrayas, J. Storch de Garcia, Tetrahedron Lett. 1997, 38, 8537-8540.
21. D. DiPetro, R. M. Borzilleri, S. M. Weinreb, J. Org. Chem. 1994, 59, 5856-5857.
22. D. A. Alonso, A. Costa, B. Mancheno, C. Najera, Tetrahedron 1997, 53, 4791-4814.
23. R. Giovannini, M. Petrini, Synlett 1997, 90-92.
24. a) C. J. M. Stirling, S. T. McDowell, J. Chem. Soc. B 1967, 343-348;
25. b) C. J. M. Stirling, S. T. McDowell, J. Chem. Soc. B 1967, 348-351.
26. H. Hirama, H. Hioki, S. Ito, C. Kubuto, Tetrahedron Lett. 1988, 29, 3121-3124.
27. A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807.
28. a) D. Enders in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, Orlando, 1984, pp. 275-339:
29. b) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173-182:
30. c) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 183-202.
31. S. Matsubara, M. Yoshioka, K. Utimoto, Chem. Lett. 1994, 827-830.
32. w = 0.046; min./max. residual electron density 0.4/+0.3e Å. The configuration at C8 was determined with respect to the known configuration at C3. Crystallographic 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-102345. Copies of the data can be obtained free of charge on application to CCDC. 12 Union Road, Cambridge CB21EZ. UK (fax: (+ 44) 1223-336-033: e-mail: deposit@ccdc.cam.ac.uk).
33. S. R. Hall, H. D. Flack, J. M. Stewart, XTAL3.2 Reference Manual. Universities of West Australia, Geneva, Maryland, Lamb, Perth, 1992.
34. Software for preparing the ball-and-stick plot representation: Ball & Stick Version 2.2. A. Falk, N. Müller, G. Schoppel, L. Webb, Linz (Austria), Stafford (UK).
35. a) J. Martens, S. Lübben, Liebigs Ann. Chem. 1990, 949-952;
36. b) S. Wilken, C. Thorey, H. Gröger, D. Haase, W. Saak, S. Pohl, J. Muzart, J. Martens, Liebigs Ann. Chem. 1997, 2133-2146, and references therein.
37. [15]
38. V. Teetz, R. Geiger, R. Henning, H. Urbach, Arzneim. Forsch. 1984, 34, 1399-1401.
39. a) H. Feuer, F. Brown, J Org. Chem. 1970, 35, 1468-1471;
40. b) H. Susuki, S Aoyagi, C. Kibayashi, J. Org. Chem. 1995, 60, 6114-6122;
41. c) N. Yamazaki, H. Suzuki, S. Aoyagi, C. Kibayashi, Tetrahedron Lett. 1996, 37, 6161-6164;
42. d) D. Enders, R. Lochtmann, Synlett 1997, 355-357.
43. a) J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549;
44. b) J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
45. 1H NMR spectroscopy from the de value of the corresponding Mosher amide).
46. All new compounds showed suitable spectroscopic data (IR, MS, NMR) and correct elemental analysis or high-resolution mass spectra.