Diastereocontrol by trialkylaluminums in the synthesis of tetrahydrofurans via radical cyclization

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3459-3462

  Ericsson, Cecilia ^a   Engman, Lars ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000234174     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016429s     Document Type: Article

References (35)

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2. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie, Band E19a. C-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989, Curran, D. P. In Comprehensive Organic Svnthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: Chichester, 1995.
3. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie, Band E19a. C-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989, Curran, D. P. In Comprehensive Organic Svnthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: Chichester, 1995.
4. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie, Band E19a. C-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989, Curran, D. P. In Comprehensive Organic Svnthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: Chichester, 1995.
5. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie, Band E19a. C-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989, Curran, D. P. In Comprehensive Organic Svnthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: Chichester, 1995.
6. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions - Concepts, Guidelines and Synthetic Applications; VCH: Weinheim, 1996. See also: Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
7. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions - Concepts, Guidelines and Synthetic Applications; VCH: Weinheim, 1996. See also: Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
8. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
9. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
10. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
11. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
12. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
13. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
14. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
15. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
16. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
17. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
18. For representative examples, see: Easton, C. J.; Merrett, M. C. Tetrahedron 1997, 53, 1151. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J. J. Org. Chem. 1994, 59, 1166. Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311. Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800. Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955. Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
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20. Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482. Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
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23. Renaud, P.; Andrau, L.; Schenk, K. Synlett 1999, 1462. Delouvrié, B.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 121, 11395. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Feldman, K. S.; Romanelli, A. L.; Ruckle, Jr, R. E.; Jean, G. J. Org. Chem. 1992, 57, 100. For a general review on the use of Lewis acids in free radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
24. Renaud, P.; Andrau, L.; Schenk, K. Synlett 1999, 1462. Delouvrié, B.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 121, 11395. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Feldman, K. S.; Romanelli, A. L.; Ruckle, Jr, R. E.; Jean, G. J. Org. Chem. 1992, 57, 100. For a general review on the use of Lewis acids in free radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
25. Renaud, P.; Andrau, L.; Schenk, K. Synlett 1999, 1462. Delouvrié, B.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 121, 11395. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Feldman, K. S.; Romanelli, A. L.; Ruckle, Jr, R. E.; Jean, G. J. Org. Chem. 1992, 57, 100. For a general review on the use of Lewis acids in free radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
26. Renaud, P.; Andrau, L.; Schenk, K. Synlett 1999, 1462. Delouvrié, B.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 121, 11395. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Feldman, K. S.; Romanelli, A. L.; Ruckle, Jr, R. E.; Jean, G. J. Org. Chem. 1992, 57, 100. For a general review on the use of Lewis acids in free radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
27. Renaud, P.; Andrau, L.; Schenk, K. Synlett 1999, 1462. Delouvrié, B.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 121, 11395. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Feldman, K. S.; Romanelli, A. L.; Ruckle, Jr, R. E.; Jean, G. J. Org. Chem. 1992, 57, 100. For a general review on the use of Lewis acids in free radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
28. Renaud, P.; Andrau, L.; Schenk, K. Synlett 1999, 1462. Delouvrié, B.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 121, 11395. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Feldman, K. S.; Romanelli, A. L.; Ruckle, Jr, R. E.; Jean, G. J. Org. Chem. 1992, 57, 100. For a general review on the use of Lewis acids in free radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
29. Renaud, P.; Andrau, L.; Schenk, K. Synlett 1999, 1462. Delouvrié, B.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Am. Chem. Soc. 1999, 121, 11395. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Feldman, K. S.; Romanelli, A. L.; Ruckle, Jr, R. E.; Jean, G. J. Org. Chem. 1992, 57, 100. For a general review on the use of Lewis acids in free radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
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34. 3Al), the reactions never did proceed to full conversion.
35. Maruoka and co-workers have reported a remarkable template effect of ATPH [aluminum tris(2,6-diphenylphenoxide)] in the preparation of 2-methyl-3-butyltetrahydrofuran by radical cyclization. In the absence of the Lewis acid, the trans isomer was formed with high selectivity (cisl trans = 3/97) whereas in the presence of ATPH the cis isomer predominated (cis/trans = 92/8). Ooi, T.; Hokke, Y.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1181.