Reductive ring opening of cis- and trans-2,3-diphenyloxirane: A common intermediate

Tetrahedron

Volumn 61, Issue 15, 2005, Pages 3865-3871

  Yus, Miguel ^a   MacIá, Beatriz ^a   Gómez, Cecilia ^a   Soler, Tatiana ^b   Falvello, Larry R ^b   Fanwick, Phillip E ^c  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

^c PURDUE UNIVERSITY   (United States)

Author keywords

1,3 Diols; DTBB catalyzed lithiation; Epoxides; Reductive ring opening

Indexed keywords

2,3 DIPHENYLOXIRANE; ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; EPIMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REDUCTION; RING OPENING; TEMPERATURE DEPENDENCE; X RAY ANALYSIS; X RAY DIFFRACTION;

EID: 15044355001     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.079     Document Type: Article

References (47)

1. For reviews, see: (a) C. Nájera, and M. Yus Trends Org. Chem. 2 1991 155 181
2. C. Nájera, and M. Yus Recent Res. Devel. Org. Chem. 1 1997 67 96
3. C. Nájera, and M. Yus Curr. Org. Chem. 7 2003 867 926
4. C. Nájera, J.M. Sansano, and M. Yus Tetrahedron 59 2003 9255 9303
5. R. Chinchilla, C. Nájera, and M. Yus Chem. Rev. 104 2004 2667 2722
6. For reviews on arene-catalyzed reactions, see: (a) M. Yus Chem. Soc. Rev. 25 1996 155 161
7. D.J. Ramón, and M. Yus Eur. J. Org. Chem. 2000 225 237
8. M. Yus Synlett 2001 1197 1205
9. M. Yus, and D.J. Ramón Lat. J. Chem. 2002 79 92
10. D.J. Ramón, and M. Yus Rev. Cubana Quim. 14 2002 75 115
11. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: Chichester, 2004; Chapter 11.
12. For mechanistic studies, see: (a) M. Yus, R.P. Herrera, and A. Guijarro Tetrahedron Lett. 42 2001 3455 3458
13. M. Yus, R.P. Herrera, and A. Guijarro Chem. Eur. J. 8 2002 2574 2584
14. M. Yus, R.P. Herrera, and A. Guijarro Tetrahedron Lett. 44 2003 1309 1312
15. M. Yus, R.P. Herrera, and A. Guijarro Tetrahedron Lett. 44 2003 1313 1316
16. M. Yus, R.P. Herrera, and A. Guijarro Tetrahedron Lett. 44 2003 5025 5027
17. For a polymer supported arene-catalyzed version of this reaction, see: (a) C. Gómez, S. Ruiz, and M. Yus Tetrahedron Lett. 39 1998 1397 1400
18. C. Gómez, S. Ruiz, and M. Yus Tetrahedron 55 1999 7017 7026
19. M. Yus, P. Candela, and C. Gómez Tetrahedron 58 2002 6207 6210
20. T. Arnauld, A.G.M. Barret, and B.T. Hopkins Tetrahedron Lett. 43 2002 1081 1083
21. For a polymer supported arene-catalyzed lithiation used in the activation of nickel, see: (e) F. Alonso, C. Gómez, P. Candela, and M. Yus Adv. Synth. Catal. 345 2003 275 279
22. C. Gómez, P. Candela, and M. Yus Russ. J. Org. Chem. 40 2004 795 801
23. For the last paper on this topic from our laboratory, see: M. Yus, R. Ortiz, and F.F. Huerta Tetrahedron 59 2003 8525 8542
24. For reviews, see: (a) M. Yus, and F. Foubelo Rev. Heteroatom Chem. 17 1997 73 107
25. M. Yus, and F. Foubelo O.A. Attanasi D. Spinelli Targets in Heterocycic Systems 2002 Italian Society of Chemistry Rome
26. M. Yus Pure Appl. Chem. 75 2003 1453 1475
27. For the last paper from our laboratory, see: M. Yus, F. Foubelo, and J.-V. Ferrández Tetrahedron 59 2003 2083 2092
28. E. Bartmann Angew. Chem., Int. Ed. Engl. 25 1986 653 654
29. J. Barluenga, J.L. Fenández-Simón, J.M. Concellón, and M. Yus J. Chem. Soc., Chem. Commun. 1987 915 916
30. J. Barluenga, J.L. Fenández-Simón, J.M. Concellón, and M. Yus J. Chem. Soc., Perkin Trans. 1 1988 3339 3343
31. T. Cohen, I.-H. Jeong, B. Mudryk, M. Bhupathy, and M.M.A. Awad J. Org. Chem. 55 1990 1528 1536
32. R.E. Conrow Tetrahedron Lett. 34 1993 5553
33. D. Behnke, L. Hennig, M. Findeisen, P. Welzel, D. Müller, M. Thormann, and H.-J. Hofmann Tetrahedron 56 2000 1081 1095
34. A. Bachki, F. Foubelo, and M. Yus Tetrahedron: Asymmetry 6 1995 1907 1910
35. A. Bachki, F. Foubelo, and M. Yus Tetrahedron: Asymmetry 7 1996 2997 3008
36. T. Soler, A. Bachki, L.R. Falvello, F. Foubelo, and M. Yus Tetrahedron: Asymmetry 9 1998 3939 3943
37. T. Soler, A. Bachki, L.R. Falvello, F. Foubelo, and M. Yus Tetrahedron: Asymmetry 11 2000 493 518
38. T. Soler, L.R. Falvello, F. Foubelo, and M. Yus Tetrahedron: Asymmetry 11 2000 2063 2066
39. T. Soler, F. Foubelo, and M. Yus Tetrahedron: Asymmetry 12 2001 801 810
40. For a preliminary communication, see: Gómez, C.; Maciá, B.; Yus, M.; Soler, T.; Falvello, L. R. 8th Electronic Conference on Synthetic Organic Chemistry (ECSOC-8), Nov 2004; Communication A002.
41. For a review, see: F. Alonso, and M. Yus Recent Res. Dev. Org. Chem. 1 1997 397 436
42. For reviews on 'Complex Induced Proximity Effect' (CIPE), see: (a) P. Beak, and A.I. Meyers Acc. Chem. Res. 19 1986 356
43. M.C. Whisler, S. MacNeil, V. Snieckus, and P. Beak Angew. Chem., Int. Ed. 43 2004 2206 2225
44. 2 hybridized carbanion in order to explain the inversion at the carbanionic carbon atom to give the thermodynamically most stable lithium intermediate and the corresponding final products 6. We think that such a planar benzylic carbanion is involved in the transformation of intermediate 8 into 5. We thank the referee for his/her comment about this aspect.
45. The proton abstraction takes probably place from the solvent (THF) by an α-deprotonation. See, for instance: J. Clayden, and S.A. Samreen New J. Chem. 26 2002 191 192 and references cited therein
46. A. Krief, and A. Nazih Tetrahedron Lett. 36 1995 8115 8118
47. R.A. Auerbach, and C.A. Kingsbury Tetrahedron 27 1971 2069 2077