Asymmetric addition reactions with optimized selenium electrophiles

Chemistry - A European Journal

Volumn 3, Issue 11, 1997, Pages 1894-1902

  Wirth, Thomas ^a   Fragale, Gianfranco ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Asymmetric synthesis; Chirality; Diselenides; Selenium

Indexed keywords

EID: 0030832656     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970031123     Document Type: Article

References (68)

1. a) E. N. Jacobsen in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, p. 159-202;
2. b) E. N. Jacobsen in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: G. Wilkmson, F. G. A. Stone, E. W. Abel, L. S. Hegedus), Pergamon, New York, 1995, ch. 11.1;
3. c) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214.
4. a) K. B. Sharpless, W. Amberg, Y. L. Benmim, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Monkawa, Z.-M. Wang, D. Xu, X.-L. Zhang, J. Org. Chem. 1992, 57, 2768-2771;
5. b) H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
6. T. Wirth, Angew. Chem. 1995, 107, 1872-1873; Angew. Chem. Int. Ed. Engl. 1995, 34, 1726-1728.
7. T. Wirth, Angew. Chem. 1995, 107, 1872-1873; Angew. Chem. Int. Ed. Engl. 1995, 34, 1726-1728.
8. a) K. C. Nicolaou, N. A. Petasis, Selenium in Natural Products Synthesis, CIS, Philadelphia, 1984;
9. b) C. Paulmier, Selenium Reagents and Intermediates in Organic Synthesis, Pergamon, Oxford, 1986;
10. c) Organoselenium Chemistry (Ed.: D. Liotta), Wiley, New York, 1987.
11. a) Y. Nishibayashi, S. K. Srivastava, H. Takada, S. Fukuzawa, S. Uemura, J. Chem. Soc. Chem. Commun. 1995, 2321-2322;
12. b) R. Déziel, E. Malenfant, J. Org. Chem. 1995, 60, 4660-4662;
13. c) K. Fujita, K. Murata, M. Iwaoka, S. Tomoda, J. Chem. Soc. Chem. Commun. 1995, 1641-1642;
14. d) T. G. Back, B. P. Dyck, ibid. 1996, 2567-2568;
15. e) K. Fujita, K. Murata, M. Iwaoka, S. Tomoda, Tetrahedron 1997, 53, 2029-2048.
16. a) T. Wirth, K. J. Kulicke, G. Fragale, J. Org. Chem. 1996, 61, 2686-2689;
17. b) T. Wirth, Liebigs Ann./Receuil 1997, 1155-1158.
18. a) P. Salama, C. Bernard, Tetrahedron Lett. 1995, 36, 5711-5714;
19. b) Y. Zhang, X. Jia, X. Zhou, Synth. Commun. 1994, 24, 1247-1252;
20. c) J.-X. Wang, W. Cui, Y. Hu, J. Chem. Soc. Perkin Trans. 1 1994, 2341-2343;
21. d) Z.-D. Liu, Z.-C. Chen, Synth. Commun. 1993, 23, 2673-2676;
22. e) L. Ping, Z. Xunjun, ibid. 1993, 23, 1721-1725;
23. f) L. Syper, J. Mlochowski, Tetrahedron 1988, 44, 6119-6130;
24. g) A. Krief, A. F. De Mahieu, W. Dumont, M. Trabelsi, Synthesis 1988, 131-133;
25. h) D. P. Thompson, P. Boudjouk, J. Org. Chem. 1988, 53, 2109-2112;
26. i) J. A. Gladysz, J. L. Hornby, J. E. Garbe, ibid. 1978, 43, 1204-1208.
27. -1) was synthesized by asymmetric reduction of the ketone (see ref. [21]).
28. N. Meyer, D. Seebach, Chem. Ber. 1980, 113, 1304-1319.
29. The ortho deprotonation of the alcohol with n = 0 was not possible and therefore the corresponding diselenide could not be synthesized.
30. 2-symmetrical diselenide with protected hydroxy groups. This diselenide adds to alkenes with good facial selectivities.
31. L. K. A. Rahman, R. M. Scrowston, J. Chem. Soc. Perkin Trans. 1 1984, 385-390.
32. R. Imwinkelried, D. Seebach, Org. Synth. 1989, 67, 180-185.
33. M. Neuburger-Zehnder, M. Neuburger, Institut für Anorganische Chemie, Universität Basel, Switzerland.
34. K. H. Schundehütte, Methoden Org. Chem. (Houben-Weyl), Vol. 10/3 (Ed.: R. Stroh), Thieme, Stuttgart, 1965, 346-355.
35. a) T. Wirth, K. J. Kulicke, G. Fragale, Helv. Chim. Acta 1996, 79, 1657-1566;
36. b) T. Wirth, Tetrahedron Lett. 1995, 36, 7849-7852.
37. a) A. Toshimitsu, H. Owada, K. Terao, S. Uemura, M. Okano, J. Chem. Soc. Perkin Trans. 1 1985, 373-378;
38. b) A. Toshimitsu, H. Owada, K. Terao, S. Uemura, M. Okano, J. Org. Chem. 1984, 49, 3796-3800.
39. N. Korber, Institut für Anorganische Chemie, Universität Bonn, Germany.
40. a) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1996, 118, 8077-8084;
41. b) H. Fujihara, T. Nakahodo, N. Furukawa, Tetrahedron Lett. 1995, 36, 6275-6278;
42. c) D. H. R. Barton, M. B. Hall, Z. Lin, S. I. Parekh, J. Reibenspies, J. Am. Chem. Soc. 1993, 115, 5056-5059;
43. d) B. M. Goldstein, S. D. Kennedy, W. J. Hennen, ibid. 1990, 112, 8265-8268;
44. e) I. Hargittai, B. Rozsondai, in The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1 (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1986, 63-155.
45. a) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1996, 118, 8077-8084;
46. b) R. Kaur, H. B. Singh, R. P. Patel, J. Chem. Soc. Dalton Trans. 1996, 2719-2726;
47. c) H. Fujihara, H. Mima, N. Furukawa, J. Am. Chem. Soc. 1995, 117, 10153-10154.
48. a) M. Srebnik, P. V. Ramachandran, H. C. Brown, J. Org. Chem. 1988, 53, 2916-2920;
49. b) H. C. Brown, J. Chandrasekharan, P. V. Ramachandran, J. Am. Chem. Soc. 1988, 110, 1539-1546.
50. -1.
51. D. L. Boger, J. S. Panek, Tetrahedron Lett. 1984, 25, 3175-3178.
52. W. Borsche, W. Scriba, Justus Liebigs Ann. Chem. 1939, 541, 283-292.
53. L. A. Elson, C. S. Gibson, J. D. A. Johnson, J. Chem. Soc. 1930, 1128-1136.
54. -1.
55. H.-G. Striegel, K. K. Mayer, W. Wiegrebe, U. P. Schlunegger, P. Siegrist, B. Aebi, Arch. Pharm. (Weinheim, Ger.) 1992, 325, 751-760.
56. -1.
57. F. F. Blicke, E. S. Blake, J. Am. Chem. Soc. 1930, 52, 235-240.
58. D. L. Romero, R. A. Morge, C. Biles, N. Berrios-Pena, P. D. May, J. Med. Chem. 1994, 37, 999-1014.
59. -1, then 30 min at 140°.
60. F. Bickelhaupt, C. Jongsma, P. de Koe, R. Lourens, N. R. Mast, G. L. van Mourik, H. Vermeer, R. J. M. Weustink, Tetrahedron 1976, 32, 1921-1930.
61. G. Koch, G. C. Lloyd-Jones, O. Loiseleur, A. Pfaltz, R. Prétôt, S. Schaffner, P. Schnider, P. von Matt, Recl. Trav. Chim. Pays-Bas 1995, 114, 206-210.
62. H.-H. Lee, S.-F. Chen, J. Chem. Soc. Perkin Trans. 1 1978, 270-274.
63. T. Wirth, U. H. Hirt, Tetrahedron Asymmetry 1997, 8, 23-26.
64. D. L. J. Clive, G. J. Chittattu, V. Farina, W. A. Kiel, S. M. Menchen, C. G. Russell, A. Singh, C. K. Wong, N. J. Curtis, J. Am. Chem. Soc. 1980, 102, 4438-4447.
65. D. L. Boger, J. S. Panek, Tetrahedron Lett. 1984, 25, 3175-3178.
66. J. Meisenheimer, P. Zimmermann, U. Kummer, Justus Liebigs Ann. Chem. 1926, 446, 205-228.
67. HPLC conditions: Chiracel OB, iPrOH hexane 5:95.
68. HPLC conditions: Chiracel OB, iPrOH hexane 15:85.