SCOPUS 정보 검색 플랫폼

Volumn 62, Issue 10, 1997, Pages 3119-3125

Synthesis of enantiopure 3-substituted pyrroline N-oxides by highly regioselective oxidation of the parent hydroxylamines: A mechanistic rationale

(5) Goti, Andrea a Cicchi, Stefano a Fedi, Valentina a Nannelli, Luca a Brandi, Alberto a

a UNIVERSITY OF FLORENCE (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030969628 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo962372p Document Type: Article

Times cited : (80)

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- For some recent examples on the synthesis and use of different chiral, enantiomerically pure, cyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467. (h) Katagiri, N.; Okada, M.; Kaneko, C.; Furuya, T. Tetrahedron Lett. 1996, 37, 1801. (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1863. (j) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861.
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56
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- For some recent examples on the synthesis and use of different chiral, enantiomerically pure, cyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467. (h) Katagiri, N.; Okada, M.; Kaneko, C.; Furuya, T. Tetrahedron Lett. 1996, 37, 1801. (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1863. (j) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861.
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57
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- For some recent examples on the synthesis and use of different chiral, enantiomerically pure, cyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467. (h) Katagiri, N.; Okada, M.; Kaneko, C.; Furuya, T. Tetrahedron Lett. 1996, 37, 1801. (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1863. (j) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861.
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58
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- For some recent examples on the synthesis and use of different chiral, enantiomerically pure, cyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467. (h) Katagiri, N.; Okada, M.; Kaneko, C.; Furuya, T. Tetrahedron Lett. 1996, 37, 1801. (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1863. (j) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861.
- (1996) Tetrahedron Lett. , vol.37 , pp. 1801
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59
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- For some recent examples on the synthesis and use of different chiral, enantiomerically pure, cyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467. (h) Katagiri, N.; Okada, M.; Kaneko, C.; Furuya, T. Tetrahedron Lett. 1996, 37, 1801. (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1863. (j) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861.
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1863
- Ishikawa, T.¹ Tajima, Y.² Fukui, M.³ Saito, S.⁴

60
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- For some recent examples on the synthesis and use of different chiral, enantiomerically pure, cyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467. (h) Katagiri, N.; Okada, M.; Kaneko, C.; Furuya, T. Tetrahedron Lett. 1996, 37, 1801. (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1863. (j) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861.
- (1996) J. Chem. Soc., Chem. Commun. , pp. 1861
- Tamura, O.¹ Gotanda, K.² Terashima, R.³ Kikuchi, M.⁴ Miyawaki, T.⁵ Sakamoto, M.⁶

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