Asymmetric synthesis of α-substituted β-amino sulfones by aza-Michael addition to alkenyl sulfones and subsequent α-alkylation

European Journal of Organic Chemistry

Volumn , Issue 6, 2000, Pages 879-892

  Enders, Dieter ^a   Müller, Stephan Frank ^a   Raabe, Gerhard ^a   Runsink, Jan ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Amines; Asymmetric synthesis; Michael addition; Sulfones; Alkylation

Indexed keywords

BENZYL BROMIDE; BETA AMINO ACID; SULFONE;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT; SYNTHESIS; X RAY ANALYSIS;

EID: 0343415171     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200003)2000:6<879::aid-ejoc879>3.0.co;2-e     Document Type: Article

References (66)

1. [1a] N. S. Simpkins, in: Sulfones in Organic Synthesis, Tetrahedron Organic Chemistry Series, Vol. 10 (Eds.: J. E. Baldwin, P. D. Magnus), Pergamon, Oxford, 1993.
2. [1b] The Chemistry of Functional Groups: The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. Stirling), Wiley, Chichester, 1988.
3. [1c] K. Schank, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1985, Vol. E11/2, p. 1132-1136.
4. [1d] T. Durst, in: Comprehensive Organic Chemistry, Vol. 3 (Eds.: D. H. R. Barton, W. D. Ollis), Pergamon, Oxford, 1979, p. 171-213.
5. [1e] N. S. Simpkins, Tetrahedron 1990, 46, 6951-6984.
6. [1f] L. Field, Synthesis 1978, 713-740.
7. [2a] M. Schäfer, K. Drauz, M. Schwarm, Methoden Org. Chem. (Houben- Weyl) 4th ed. 1995, vol. E21/5, pp. 5588-5642.
8. [2b] 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.
9. [2c] D. Enders, H. Wahl, W. Bettray, Angew. Chem. 1995, 107, 527-529; Angew. Chem. Int. Ed. Engl. 1995, 34, 527-529, and references cited therein.
10. [2c] D. Enders, H. Wahl, W. Bettray, Angew. Chem. 1995, 107, 527-529; Angew. Chem. Int. Ed. Engl. 1995, 34, 527-529, and references cited therein.
11. [3a] D. Braghiroli, R. Avallone, M. D. Di Bella, Tetrahedron: Asymmetry 1997, 8, 2209-2213.
12. [3b] H. Nakamura, H. Wu, J. Kobayashi, M. Kobayashi, Y. Ohizumi, Y. Hirata, J. Org. Chem. 1985, 50, 2494-2497.
13. [3c] Y. Ichikawa, Tetrahedron Lett. 1988, 29, 4957-4958.
14. [3d] B. Beagley, P. H. Crackett, R. G. Pritchard, R. J. Stoodley, J. Chem. Soc., Perkin Trans. 1 1990, 773-781.
15. [3e] Y. Girard, M. Larue, T. R. Jones, J. Rokach, Tetrahedron Lett. 1982, 23, 1023-1026.
16. N. A. Sasaki, M. Dockner, A. Chiaroni, C. Riche, P. Potier, J. Org. Chem. 1997, 62, 765-770, and references cited therein.
17. R. Pauly, A. Sasaki, P. Portier, Tetrahedron Lett. 1994, 35, 237-240.
18. M. Hirama, H. Hioki, S. Ito, Tetrahedron Lett. 1988, 29, 3125-3128.
19. J. de Blas, J. C. Carretero, E. Domínguez, Tetrahedron Lett. 1994, 35, 4603-4606.
20. J. C. Wu, T. Pathak, W. Tong, J. M. Vial, G. Remaud, J. Chattopadhyaya, Tetrahedron 1988, 44, 6705-6722.
21. [9a] J. C. Carretero, R. G. Arrayás, Synlett 1999, 49-52.
22. [9b] J. de Vincente, R. G. Arrayás, J. C. Carretero, Tetrahedron Lett. 1999, 40, 6083-6086.
23. [9c] J. C. Carretero, R. G. Arrayás, J. S. de Garcia, Tetrahedron Lett. 1997, 38, 8537-8540.
24. D. DiPetro, R. M. Borzilleri, S. M. Weinreb, J. Org. Chem. 1994, 59, 5856-5857.
25. D. A. Alonso, A. Costa, B. Mancheño, C. Najerá, Tetrahedron 1997, 53, 4791-4814.
26. R. Giovannini, M. Petrini, Synlett 1997, 90-92.
27. [13a] R. Tanikaga, N. Shibata, T. Yoneda, J. Chem. Soc., Perkin Trans. 1 1997, 2253-2257.
28. [13b] R. V. M. Campbell, L. Crombie, D. Findley, R. W. King, G. Pattenden, D. A. Whiting, J. Chem. Soc., Perkin Trans. 1 1975, 897-913.
29. Recent examples: [14a] D. W. Knight, A. W. Sibley, J. Chem. Soc., Perkin Trans. 1 1997, 2179-2187.
30. [14b] D. J. Hart, J. Li, W.-L. Wu, A. P. Kozikowski, J. Org. Chem. 1997, 62, 5023-5033.
31. [14c] N. Magnus, P. Magnus, Tetrahedron Lett. 1997, 38, 3491-3494.
32. [14d] A. Solladié-Cavallo, D. Roche, J. Fischer, A. De Cian, J. Org. Chem. 1996, 61, 2690-2694.
33. [14e] I. E. Markó, F. Murphy, S. Dolan, Tetrahedron Lett. 1996, 37, 2089-2092.
34. Recent examples: [15a] H. Tanimoto, T. Oritani, Tetrahedron 1997, 53, 3527-3536.
35. [15b] D. A. Alonso, L. R. Falvello, B. Mancheño, C. Nájera, M. Tomás, J. Org. Chem. 1996, 61, 5004-5012.
36. [15c] P. Bonete, C. Nájera, Tetrahedron 1996, 52, 4111-4122.
37. [15d] T. A. Houston, M. Koreeda, Synth. Commun. 1994, 24, 393-398.
38. [15e] S. H. Pine, G. Shen, J. Bautista, C. Sutton, Jr., W. Yamada, L. Apodaca, J. Org. Chem. 1990, 55, 2234-2237
39. [15f] M. Isobe, J. Obeyama, Y. Funabashi, T. Goto, Tetrahedron Lett. 1988, 29, 4773-4776.
40. [16a] C. J. M. Stirling, S. T. McDowell, J. Chem. Soc. B 1967, 343-348.
41. [16b] C. J. M. Stirling, S. T. McDowell, J. Chem. Soc. B 1967, 348-351.
42. H. Hirama, H. Hioki, S. Ito, C. Kubuto, Tetrahedron Lett. 1988, 29, 3121-3124.
43. A. Padwa, B. H. Norman, J. Org. Chem. 1990, 55, 4801-4807.
44. S. Matsubara, M. Yoshioka, K. Utimoto, Chem. Lett. 1994, 827-830.
45. H. Eichenauer, Ph. D. Dissertation, Justus-Liebig-Universität Gießen, 1980.
46. [21a] D. Enders, H. Eichenauer, Chem. Ber. 1979, 112, 2933-2960.
47. [21b] D. Enders in Asymmetric Synthesis, Vol. 3B (Hrsg.: J. D. Morrison), Academic Press, Orlando, 1984, p. 275-339.
48. [21c] D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173-182; 183-202.
49. [22a] D. Enders, H. Kipphardt, P. Gerdes, L. J. Breña-Valle, V. Bhushan, Bull. Soc. Chim. Belg. 1988, 97, 691-704.
50. [22b] D. Enders, Acros Organics Acta 1995, 1, 35-36.
51. [23a] J. Martens, S. Lübben, Liebigs Ann. Chem. 1990, 949-952.
52. [23b] J. Wilken, C. Theorey, H. Gröger, D. Haase, W. Saak, S. Pohl, J. Muzart, J. Martens, Liebigs Ann. Chem. 1997, 2133-2146, and references cited therein.
53. H. Kempen, Ph. D. Dissertation, RWTH Aachen, 1994.
54. M. W. Rathke, M. Nowak, J. Org. Chem. 1985, 50, 2624-2626.
55. D. Enders, S. F. Müller, G. Raabe, Angew. Chain. 1999, 111, 212-214; Angew. Chem. Int. Ed. 1999, 38, 195-197.
56. D. Enders, S. F. Müller, G. Raabe, Angew. Chain. 1999, 111, 212-214; Angew. Chem. Int. Ed. 1999, 38, 195-197.
57. S. R. Hall, H. D. Flack, J. M. Stewart, XTAL3.2 Reference Manual, Universities of West Australia, Geneva, Maryland, Lamb, Perth, 1992.
58. 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).
59. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-102345 and CCDC-115145. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: (internat.) +44-1223/336-033, E-mail: deposit@ccdc.cam.ac.uk).
60. Preparation analogous to that of SAMP (S)-2. See ref. [21]
61. V. Teetz, R. Geiger, R. Henning, H. Urbach, Arzneim. Forsch. 1984, 34, 1399-1401.
62. D. Enders, R. Lochtman, M. Meiers, S. F. Müller, R. Lazny, Synlett 1998, 1182-1184.
63. [33a] J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549.
64. [33b] J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
65. The starting material for the synthesis of RAMBO (5) -(R,R,R)-azabicyclo[3.3.0]octane-3-carboxylic acid benzyl ester hydrochloride, which was supplied by the former Hoechst AG - showed an ee value of 80% (determined by NMR spectroscopy from the de value of the corresponding Mosher amide).
66. D. Enders, S. F. Müller, G. Raabe, Synlett 1999, 741-743.