Stereoselective synthesis of 4-(N-mesylamino)-2,3-unsaturated-α-O- glycosides via a new glycal-derived vinyl α-N-(mesyl)-aziridine

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1299-1302

  Di Bussolo, Valeria ^a   Romano, Maria Rosaria ^a   Pineschi, Mauro ^a   Crotti, Paolo ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AZIRIDINE DERIVATIVE; BENZENE; DISACCHARIDE; GLYCOSIDE; MESYLIC ACID DERIVATIVE; MONOSACCHARIDE; PHENOL DERIVATIVE; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

AZIRIDINES; CYCLIZATION; GLYCOSIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 17444398650     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050053r     Document Type: Article

References (33)

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13. Actually, the N-acetyl-O-mesyl deivative 6-Ac corresponding to N,O-dimesylate 6 (Scheme 2) was initially prepared as a suitable precursor of the N-acetyl aziridine (7α-Ac) corresponding to 7α and examined in addition reaction with alcohols. Unfortunately, 6-Ac turned out to be completely unreactive with alcohols under protocol B (see text) and was entirely recovered from the reaction mixture. 1,4-Addition products derived from the corresponding aziridine 7α-Ac were obtained, even if in an unsatisfactory yield, only when 6-Ac was left to react under protocol A (see text) only with MeOH and EtOH.
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18. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
19. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
20. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
21. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
22. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
23. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
24. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
25. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
26. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
27. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
28. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
29. For reviews on aziridine chemistry, see: (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (b) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. (c) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599. For synthesis of activated vinylaziridines, see: (d) Arini, L. G.; Sinclair, A.; Szeto, P.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 1589. (e) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377. (f) Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516. (g) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999. (h) Åhman, T.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148 and references therein. For synthetic applications and ring-opening reactions of sugar aziridines, see: (i) Hale, K. J.; Domostoj, M. M.; Tocher, D. A.; Irving, E.; Scheinmann, F. Org. Lett. 2003, 5, 2927. (j) Charon, D.; Mondange, M.; Pons, J.-F.; Le Blay, K.; Chaby, R. Bioorg. Med. Chem. 1998, 6, 755. (k) Ali, Y.; Richardson, A. C.; Gibbs, C. F.; Hough, L. Carbohydr. Res. 1968, 7, 255. (l) Gibbs, C. F.; Hough, L.; Richardson, A. C. Carbohydr. Res. 1965, 1, 290. (m) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1965, 3828. (n) Buss, D. H.; Hough, L.; Richardson, A. C. J. Chem. Soc. 1965, 2736.
30. Prolonged reaction times (1 h) at 5°C afforded a 7:3 mixture of vinyl aziridine 7α and tert-butyl α-O-glycoside 11α (Table 1) derived from 1,4-addition to aziridine 7α of t-BuOH formed in the reaction mixture by deprotonation-cyclization of N,O-dimesylate 6 by t-BuOK.
31. 1H NMR).
32. 1H NMR spectrum of both 8β and 9β (δ 2.95) is more downfield than that in the corresponding anomers 8α and 9α (δ 2.88). As a consequence, the observed value of the chemical shift of the mesyl group for the main or almost unique addition product, typically around δ 2.87-2.90, together with the observation of the constant presence of a slightly downfield singlet signal around δ 2.95-2.98 in the crude addition reaction mixture corresponding to entries 3-8, Table 1, reasonably due to the corresponding β-anomer (5-7% in entries 3 and 5, and less than 1% in entries 4 and 6-8, Table 1) made it possible to assign the α-configuration to the main, or almost unique product, in each addition reaction.
33. Overberger, C. G.; Tobkes, M. J. Polym. Sci. 1964, 2, 2481.