A combined, 6-exo-dig radical cyclization-palladium catalyzed allylic amination, approach to aminocarbasugar analogs: Synthesis of novel N-substituted aminocyclitols from D-mannose

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7863-7866

  Gómez, Ana M ^a   Moreno, Eduardo ^a   Valverde, Serafín ^a   Lopez J Cristobal ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOCYCLITOL; CARBOHYDRATE DERIVATIVE; MANNOSE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0037190870     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01919-6     Document Type: Article

References (46)

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14. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
15. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
16. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
17. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
18. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
19. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
20. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
21. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
22. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
23. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
24. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
25. Selected synthesis of aminocyclitols, aminocarbasugars and analogs: (a) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335; (b) Gravier-Pelletier, C.; Maton, W.; Lecourt, T.; Le Merrer, Y. Tetrahedron Lett. 2001, 42, 4475; (c) Ogawa, S.; Sekura, R.; Maruyama, A.; Yuasa, H.; Hashimoto, H. Eur. J. Org. Chem. 2000, 2089; (d) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307; (e) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129; (f) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853; (g) Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett. 1997, 38, 1407; (h) Kameda, Y.; Kawashima, K.; Takeuchi, M.; Ikeda, K.; Asano, N.; Matsui, K. Carbohydr. Res. 1997, 300, 259; (i) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Synthesis, 1997, 925; (j) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332; (k) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419; (l) Letellier, P.; Ralainairina, R.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1994, 35, 4555.
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39. 3SnH (1.6 equiv.) and AIBN (0.1 equiv.) in toluene (5 mL/mmol) was then added and the reaction mixture was kept at that temperature over 12 h. After cooling, the organic solvent was evaporated and the residue was purified by flash chromatography.
40. The configuration at C-5 in compounds 12 has been rigorously confirmed by their correlation with previously described carbasugars of known absolute configuration: Gomémez, A. M.; Moreno, E.; Valverde, S.; López, J. C. Tetrahedron Lett. 2002, 44, 5559. The corresponding C-5-6-epi derivative (as an epimeric mixture at C-1) was also detected, albeit in low yield (<5%).
41. 3 (76 mg, 0.29 mmol), and the corresponding amine 13 (0.38 mmol) were added. The reaction was then heated to 85°C for the time indicated in Table 1 . After cooling, the organic solvent was evaporated and the residue dissolved in ethyl acetate and washed with water. The organic layer was then dried (sodium sulfate) and evaporated to furnish a residue, which was purified by flash chromatography using hexane:ethyl acetate mixtures as eluent.
42. 5: C, 63.69; H, 8.61; N, 4.13. Found: C, 63.82; H, 8.52; N, 3.97.
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