Moisture Stable Promoters for Selective α-Fucosylation Reactions: Synthesis of Antigen Fragments

Synlett

Volumn , Issue 2, 2004, Pages 275-278

  Adinolfi, Matteo ^a   Iadonisi, Alfonso ^a   Ravidà, Alessandra ^a   Schiattarella, Marialuisa ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Acid washed molecular sieves; Carbohydrates; Stereoselectivity in fucosylation reactions; Synthesis of oligosaccharides; Ytterbium triflate

Indexed keywords

ANTIGEN; ETHER; REAGENT; SOLVENT;

ACETYLATION; AMINO ACID SEQUENCE; ARTICLE; BENZYLATION; FUCOSYLATION; MOISTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 1242341274     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815415     Document Type: Article

References (45)

1. Ernst, B.; Hart, G. W.; Sinaÿ, P. Carbohydrates in Chemistry and Biology; Wiley-VCH: Weinheim, 2000.
2. For a discussion on the problems related to α-fucosylations and pertinent references see: (a) Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545. (b) Love, K. R.; Andrade, R. B.; Seeberger, P. H. J. Org. Chem. 2001, 66, 8165.
3. For a discussion on the problems related to α-fucosylations and pertinent references see: (a) Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545. (b) Love, K. R.; Andrade, R. B.; Seeberger, P. H. J. Org. Chem. 2001, 66, 8165.
4. For other recent examples see: (a) Manzoni, L.; Lay, L.; Schmidt, R. R. J. Carbohydr. Chem. 1998, 17, 739. (b) Xia, J.; Alderfer, J. L.; Piskorz, C. F. ; Matta, K. L. Chem.-Eur. J. 2000, 6, 3442. (c) Söderman, P.; Larsson, E. A.; Wilman, G. Eur. J. Org. Chem. 2002, 1614. (d) Ando, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 2003, 338, 503. (e) Xia, J.; Alderfer, J. L.; Locke, R. D.; Piskorz, C. F.; Matta, K. L. J. Org. Chem. 2003, 68, 2752.
5. For other recent examples see: (a) Manzoni, L.; Lay, L.; Schmidt, R. R. J. Carbohydr. Chem. 1998, 17, 739. (b) Xia, J.; Alderfer, J. L.; Piskorz, C. F. ; Matta, K. L. Chem.-Eur. J. 2000, 6, 3442. (c) Söderman, P.; Larsson, E. A.; Wilman, G. Eur. J. Org. Chem. 2002, 1614. (d) Ando, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 2003, 338, 503. (e) Xia, J.; Alderfer, J. L.; Locke, R. D.; Piskorz, C. F.; Matta, K. L. J. Org. Chem. 2003, 68, 2752.
6. For other recent examples see: (a) Manzoni, L.; Lay, L.; Schmidt, R. R. J. Carbohydr. Chem. 1998, 17, 739. (b) Xia, J.; Alderfer, J. L.; Piskorz, C. F. ; Matta, K. L. Chem.-Eur. J. 2000, 6, 3442. (c) Söderman, P.; Larsson, E. A.; Wilman, G. Eur. J. Org. Chem. 2002, 1614. (d) Ando, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 2003, 338, 503. (e) Xia, J.; Alderfer, J. L.; Locke, R. D.; Piskorz, C. F.; Matta, K. L. J. Org. Chem. 2003, 68, 2752.
7. For other recent examples see: (a) Manzoni, L.; Lay, L.; Schmidt, R. R. J. Carbohydr. Chem. 1998, 17, 739. (b) Xia, J.; Alderfer, J. L.; Piskorz, C. F. ; Matta, K. L. Chem.-Eur. J. 2000, 6, 3442. (c) Söderman, P.; Larsson, E. A.; Wilman, G. Eur. J. Org. Chem. 2002, 1614. (d) Ando, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 2003, 338, 503. (e) Xia, J.; Alderfer, J. L.; Locke, R. D.; Piskorz, C. F.; Matta, K. L. J. Org. Chem. 2003, 68, 2752.
8. For other recent examples see: (a) Manzoni, L.; Lay, L.; Schmidt, R. R. J. Carbohydr. Chem. 1998, 17, 739. (b) Xia, J.; Alderfer, J. L.; Piskorz, C. F. ; Matta, K. L. Chem.-Eur. J. 2000, 6, 3442. (c) Söderman, P.; Larsson, E. A.; Wilman, G. Eur. J. Org. Chem. 2002, 1614. (d) Ando, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 2003, 338, 503. (e) Xia, J.; Alderfer, J. L.; Locke, R. D.; Piskorz, C. F.; Matta, K. L. J. Org. Chem. 2003, 68, 2752.
9. (a) Schmid, U.; Waldmann, H. Chem.-Eur. J. 1998, 4, 494.
10. (b) Böhm, G.; Waldmann, H. Tetrahedron Lett. 1995, 36, 3843.
11. Schmidt, R. R.; Toepfer. A. Tetrahedron Lett. 1991, 32, 3353.
12. Flowers, H. M. Carbohydr. Res. 1983, 119, 75.
13. (a) Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056.
14. (b) Sato, S.; Mori, M.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1986, 155, C6.
15. (a) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Schiattarella, M. Tetrahedron Lett. 2001, 42, 5967.
16. (b) Adinolfi, M.; Barone, G.; Iadonisi, A.; Schiattarella, M. Tetrahedron Lett. 2002, 43, 5573.
17. (c) Adinolfi, M.; Iadonisi, A.; Schiattarella, M. Tetrahedron Lett. 2003, 44, 6479.
18. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
19. Yu, B.; Tao, H. Tetrahedron Lett. 2001, 42, 2405.
20. For a recent review on the synthesis of 1,2-cis-glycosides: Demchenko, A. Synlett 2003, 1225.
21. Adinolfi, M.; Barone, G.; Iadonisi, A.; Schiattarella, M. Org. Lett. 2003, 5, 987.
22. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
23. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
24. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
25. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
26. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
27. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
28. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
29. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
30. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
31. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
32. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
33. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
34. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
35. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
36. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
37. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
38. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
39. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
40. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
41. 3a,3e. For further examples see: (a) Jacquinet, J.-C.; Sinaÿ, P. J. Chem. Soc., Perkin Trans. 1 1979, 314. (b) Hindsgaul, O.; Norberg, T.; Pendu, J. L.; Lemieux, R. U. Carbohydr. Res. 1982, 109, 109. (c) Lonn, H. Carbohydr. Res. 1985, 139, 115. (d) Nillsson, M.; Norberg, T. Carbohydr. Res. 1988, 183, 71. (e) Sato, S.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 5267. (f) Classon, B.; Garegg, P. J.; Heiland, A.-C. J. Carbohydr. Chem. 1989, 8, 543. (g) Nillsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613. (h) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 870. (i) Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161. (j) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843. (k) Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res. 1994, 263, C1. (l) vom de Brook, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 101. (m) Jain, R. K.; Vig, R.; Locke, R. D.; Mohammad, A.; Matta, K. L. Chem. Commun. 1996, 65. (n) Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. (o) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173. (p) Figueroa-Perez, S.; Verez-Bencomo, V. Tetrahedron Lett. 1998, 39, 9143. (q) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314. (r) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111. (s) Gege, C.; Oscarson, S.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 377. (t) Majumdar, D.; Zhu, T.; Boons, G.-J. Org. Lett. 2003, 5, 3591.
42. Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053.
43. 3N were added. The mixture was filtered on a short pad of silica gel, concentrated, and the residue purified by silica gel chromatography (eluent: hexane/EtOAc mixtures).
44. Procedure B: A mixture of acceptor (0.2 mmol) and donor 2 (see Table 1 for relative amounts) were coevaporated three times in anhyd toluene and the residue was kept under vacuum for 1 h. Acid washed molecular sieves (4 Å AW 300 MS, pellets, 1.5-2 g) were then added and the solvent (dichloroethane or toluene, 2-4 mL) was added at 0°C. The mixture was kept at 0°C under stirring for 30 min and then temperature was left to rise spontaneously. After complete consumption of the donor (24-36 h), the mixture was filtered through a cotton pad and concentrated. The residue was purified by silica gel chromatography (eluent: hexane/ EtOAc mixtures).
45. 2]; other signals at δ = 80.5, 74.8, 74.6, 74.4, 73.6, 73.2, 73.1, 72.3, 72.0, 71.8, 70.3, 67.9, 67.8, 64.5, 61.8.