Selenylated dienes: synthesis, stereochemical studies by 77Se NMR, and transformation into functionalized allenes

Tetrahedron

Volumn 63, Issue 18, 2007, Pages 3707-3717

  Redon, Sebastien ^a   Berthe Berkaoui, Anne Lise ^a   Pannecoucke, Xavier ^a   Outurquin, Francis ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

Allenes; Conjugated dienes; Oxidation; Selenium

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKADIENE; ALLENE DERIVATIVE; CARBAMIC ACID DERIVATIVE; SELENIMIDE DERIVATIVE; SELENIUM 77; SELENIUM DERIVATIVE; SELENOXIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; HORNER WADSWORTH EMMONS REACTION; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 33947695745     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.082     Document Type: Article

References (73)

1. Wirth T. Organoselenium Chemistry: Modern developments in Organic Synthesis. Topics in Current Chemistry Vol. 208 (2000), Springer, Berlin, Heidelberg
2. Back T.G. Organoselenium Chemistry: A Practical Approach (1999), Oxford University Press, New York, NY
3. Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis (1986), Pergamon, Oxford
4. Liotta D.C. Organoselenium Chemistry (1987), Wiley, New York, NY
5. Patai S. The Chemistry of Organic Selenium and Tellurium Compounds Vols. 1 and 2 (1987), Wiley, New York, NY
6. Wirth T. Angew. Chem., Int. Ed. Engl. 34 (1995) 1726-1728
7. Wirth T. Tetrahedron 55 (1999) 1-28
8. Wirth T. Angew. Chem., Int. Ed. 39 (2000) 3742-3751
9. Browne D.M., and Wirth T. Curr. Org. Chem. 10 (2006) 1893-1903
10. Franck X., Langlois E., and Outurquin F. Synthesis (2007) 719-724
11. Bowman W.R., Bridge C.F., and Brookes P. J. Chem. Soc., Perkin Trans. 1 (2000) 1-14
12. Renaud P., Andrau L., and Schenk L. Synlett (1999) 1462-1464
13. Zhang J., and Clive D.L.J. J. Org. Chem. 64 (1999) 770-779
14. Ogawa A., Ogawa I., Obayashi R., Umezu K., Doi M., and Hirao T. J. Org. Chem. 64 (1999) 86-92
15. Crich D., and Mo X.S. J. Am. Chem. Soc. 120 (1998) 8298-8304
16. Byers J.H., Shaughnessy E.H., and Mackie T.N. Heterocycles 48 (1998) 2071 and references cited therein
17. Paulmier C., Outurquin F., and Plaquevent J.C. Tetrahedron Lett. 29 (1988) 5889-5892
18. Paulmier C., Outurquin F., and Plaquevent J.C. Tetrahedron Lett. 29 (1988) 5893-5896
19. Outurquin F., and Paulmier C. Tetrahedron Lett. 29 (1989) 690-691
20. Duclos J.F., and Paulmier C. Tetrahedron Lett. 34 (1993) 7417-7420
21. Ponthieux S., Outurquin F., and Paulmier C. Tetrahedron Lett. 36 (1995) 6453-6456
22. Ponthieux S., Outurquin F., and Paulmier C. Tetrahedron Lett. 51 (1995) 9569-9580
23. Lerouge P., and Paulmier C. Bull. Soc. Chim. Fr. (1985) 1225-1229
24. Lerouge P., and Paulmier C. Tetrahedron Lett. 25 (1984) 1987-1990
25. Bridges A.J., and Fischer J.W. Tetrahedron Lett. 24 (1983) 447-450
26. Liotta C.L., and Verbicky Jr. J.W. Tetrahedron Lett. 26 (1985) 1395-1398
27. Roversi E., Monnat F., Vogel P., Schenk K., and Roversi P. Helv. Chim. Acta 85 (2002) 733-760
28. Bates G.S., Fryzuk M.D., and Stone C. Can. J. Chem. 65 (1987) 2612-2617
29. Comasseto J.V., and Brandt C.A. Synthesis (1987) 146-149
30. Zhu L.-S., Huang Z.-Z., and Huang X. Tetrahedron 52 (1996) 9819-9822
31. Ma Y., and Huang X. J. Chem. Soc., Perkin Trans. 1 (1997) 2953-2955
32. Cai M.-Z., Huang J.-D., and Peng C.-Y. J. Organomet. Chem. 681 (2003) 98-101
33. Lerouge P., and Paulmier C. Bull. Soc. Chim. Fr. (1985) 1219-1224
34. Paulmier C., and Lerouge P. Tetrahedron Lett. 23 (1982) 1557-1960
35. Blatcher P., and Warren S. J. Chem. Soc., Perkin Trans. 1 (1985) 1055-1066
36. Pearson W.H., Lin K.-C., and Poon Y.-F. J. Org. Chem. 54 (1989) 5814-5819
37. Voyle M., Kyler K.S., Arseniyadis S., Dunlap N.K., and Watt D.S. J. Org. Chem. 48 (1983) 470-476
38. Squillacote M.E., and Liang F. J. Org. Chem. 70 (2005) 6564-6573
39. In: Patai S. (Ed). The Chemistry of Ketenes, Allenes, and Related Compounds (1980), John Wiley and Sons, Chichester, UK
40. Brandsma L., and Verkruijsse H.D. Synthesis of Acetylenes, Allenes, and Cumulenes (1981), Elvesier, Amsterdam
41. In: Landor S.R. (Ed). The Chemistry of the Allenes (1983), Academic, London
42. Schuster H., and Coppola G. Allenes in Organic Synthesis (1984), John Wiley and Sons, New York, NY
43. Pasto D.J. Tetrahedron 40 (1984) 2805-2827
44. In: Krause N., and Hashmi A.S.K. (Eds). Modern Allene Chemistry (2004), Wiley-VCH, Weinheim
45. Yamamoto Y., and Radhakrishnan U. Chem. Soc. Rev. 28 (1999) 199-207
46. Hashmi A.S.K. Angew. Chem., Int. Ed. 39 (2000) 3590-3593
47. Zimmer R., Dinesh C.U., Nandanan E., and Khan F.A. Chem. Rev. 100 (2000) 3067-3125
48. Ohno H. Chem. Pharm. Bull. 53 (2005) 1211-1226
49. Krause N., Laux M., and Hoffmann-Röder A. Tetrahedron Lett. 41 (2000) 9613-9616
50. Krause N., and Hoffmann-Röder A. Tetrahedron 60 (2004) 11671-11694
51. Perepelkin O.V., Cherkasov L.N., Korner V.A., Bal'yan K.V., and Petrov A.A. Zh. Obshch. Khim. 35 (1965) 574-578
52. Cowie J.S., Landor P.D., and Landor S.R. J. Chem. Soc., Perkin Trans. 1 (1973) 720-724
53. Alexakis A., Marek I., Mangeney P., and Normant J.F. Tetrahedron 47 (1991) 1677-1696
54. Marshall J.A., Robinson E.D., and Zapata A. J. Org. Chem. 54 (1989) 5854-5855
55. Marshall J.A., and Wang X.J. J. Org. Chem. 55 (1990) 2995-2996
56. Marshall J.A., and Wang X.J. J. Org. Chem. 56 (1991) 4913-4918
57. Katsuhira T., Harada T., and Oku A. J. Org. Chem. 59 (1994) 4010-4014
58. Vinson N.A., Day C.S., and Welker M.E. Organometallics 19 (2000) 4356-4368
59. Shi L., Xia W., Yang J., Wen X., and Huang Y.Z. Tetrahedron Lett. 28 (1987) 2155-2158
60. Horváth A., and Bäckvall J.-E. J. Org. Chem. 66 (2001) 8120-8126
61. Trost B.M., Jonasson C., and Wuchrer M. J. Am. Chem. Soc. 123 (2001) 12736-12737
62. Halliday R.P., Davis C.S., Heotis J.P., Pals D.T., Watson E.J., and Bickerton R.K. J. Pharm. Sci. 57 (1968) 430-433
63. Krantz A., Kokel B., Sachdeva Y.P., Salach J., Claesson A., and Sahlberg C. In: Kalman (Ed). Drug Action and Design: Mechanism-based Enzyme Inhibitors (1979), Elsevier, North Holland 145
64. Monoamine Oxidase and its Inhibitors; Ciba Foundation Symposium 39; Elsevier: North Holland, 1976.
65. Singer T.P., Von Korf R.W., and Murphy D.L. Monoamine Oxidase, Structure Function and Altered Functions (1979), Academic, New York, NY
66. Frankhauser J.E., Peevey R.M., and Hopkins P.B. Tetrahedron Lett. 25 (1984) 15-18
67. Shea R.G., Fitzner J.N., Frankhauser J.E., and Hopkins P.B. J. Org. Chem. 49 (1984) 3647-3650
68. Fitzner J.N., Shea R.G., Frankhauser J.E., and Hopkins P.B. J. Org. Chem. 50 (1985) 417-419
69. Spaltenstein A., Carpino P.A., and Hopkins P.B. Tetrahedron Lett. 27 (1986) 147-150
70. Shea R.G., Fitzner J.N., Frankhauser J.E., Spaltenstein P.A., Peevey R.M., Pratt D.V., Tenge B.J., and Hopkins P.B. J. Org. Chem. 51 (1986) 5243-5252
71. Spaltenstein A., Carpino P.A., Miyake F., and Hopkins P.B. J. Org. Chem. 52 (1987) 3759-3766
72. Krijnen E.S., Zuilhof H., and Lodder G. J. Org. Chem. 59 (1994) 8139-8150
73. Peaks appeared as doublet due to diastereomeric mixtures.