Lewis acids in diastereoselective processes involving acyclic radicals

Pure and Applied Chemistry

Volumn 68, Issue 1, 1996, Pages 89-96

  Guindon, Yvan ^a,c   Guérin, Brigitte ^c   Rancourt, Jean ^b   Chabot, Catherine ^b   Mackintosh, Nicole ^b   Ogilvie, W W ^b  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b BOEHRINGER INGELHEIM CANADA LTD   (Canada)

^c CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002535530     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668010089     Document Type: Article

References (43)

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20. Monodentate: a) P. Renaud, N. Moufid, L.H. Kuo and D.P. Curran. J. Org. Chem. 59, 3547 (1994). b) P. Renaud and M. Ribezzo, J. Amer. Chem. Soc. 113, 7803 (1991). c) D.P. Curran and L.H. Kuo. J. Org. Chem. 59, 3259 (1994). d) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida and N. Kawahara. J. Amer. Chem. Soc. 116, 6455 (1994). e) M. Nishida, H. Hayashi, Y. Yamaura, E. Yanaginuma and O. Yonemitsu. Tetrahedron Lett. 32, 269 (1995).
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23. Bidentate: a) Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Homer and J. Rancourt. J. Amer. Chem. Soc. 113, 9701 (1991). b) Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh and W.W. Ogilvie. Synlett, 449 (1995). c) T. Toru, Y. Watanabe, M. Tsusaka and Y. Ueno. J. Amer. Chem. Soc. 115, 10464 (1993). d) H. Nagano and Y. Kuno. J. Chem. Soc., Chem. Commun. 987 (1994). e) Y. Yamamoto, S. Onuki, M. Yumoto and N. Asao. J. Amer. Chem. Soc. 116, 421 (1994).
24. Bidentate: a) Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Homer and J. Rancourt. J. Amer. Chem. Soc. 113, 9701 (1991). b) Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh and W.W. Ogilvie. Synlett, 449 (1995). c) T. Toru, Y. Watanabe, M. Tsusaka and Y. Ueno. J. Amer. Chem. Soc. 115, 10464 (1993). d) H. Nagano and Y. Kuno. J. Chem. Soc., Chem. Commun. 987 (1994). e) Y. Yamamoto, S. Onuki, M. Yumoto and N. Asao. J. Amer. Chem. Soc. 116, 421 (1994).
25. Bidentate: a) Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Homer and J. Rancourt. J. Amer. Chem. Soc. 113, 9701 (1991). b) Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh and W.W. Ogilvie. Synlett, 449 (1995). c) T. Toru, Y. Watanabe, M. Tsusaka and Y. Ueno. J. Amer. Chem. Soc. 115, 10464 (1993). d) H. Nagano and Y. Kuno. J. Chem. Soc., Chem. Commun. 987 (1994). e) Y. Yamamoto, S. Onuki, M. Yumoto and N. Asao. J. Amer. Chem. Soc. 116, 421 (1994).
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38. The number of equivalents reported is relative to the number of mmoles of substrate normally used. This was kept constant for entries 1 through 4.
39. +2 in solution nor the allylation ratio.
40. 3B. The reaction proceeded normally without changes to the yield nor to the level of diastereoselectivity. This indicates that the insoluble material does not participate in the reaction after the pre-equilibration phase.
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43. We have obtained different results when reductions are considered, the monodentate complex reacting faster than the bidentate complex.