Synthesis of highly oxygenated enantiomerically pure cis-bicyclo[4.3.0]nonanes from secondary sugar allyltin derivatives

Tetrahedron Asymmetry

Volumn 14, Issue 12, 2003, Pages 1709-1713

  Jarosz, Sławomir ^a   Szewczyk, Katarzyna ^a   Zawisza, Anna ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF LODZ   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; BICYCLO COMPOUND; CARBOHYDRATE DERIVATIVE; MESYLIC ACID DERIVATIVE; ORGANOTIN COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; GEOMETRY; METHODOLOGY; OXYGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 0037529981     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00310-0     Document Type: Article

References (22)

1. Preliminary communication: Jarosz S., Szewczyk K. Tetrahedron Lett. 42:2001;3021-3024.
2. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
3. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
4. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
5. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
6. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
7. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
8. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
9. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
10. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
11. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
12. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
13. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
14. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
15. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
16. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
17. For examples of the application of IMDA in the synthesis of carbobicyclic products, see: (a) Fraser-Reid, B.; Benko, Z.; Guiliano, R.; Sun, K. M.; Taylor, N. J. Chem. Soc., Chem. Commun. 1984, 1029-1030; (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Tetrahedron Organic Chemistry Series Vol. 8) 1990, 91-208; (c) Roush, W. R. Advances in Cycloaddition 1990, 2, 91-146 (Curran, D. P., Ed.) and references cited therein; (d) Herczegh, P.; Zsely, M.; Szilagyi, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Organic Chemistry 1992, 112 (ACS Symposium Series 494, Guiliano, R. M., Edition); (e) Kozikowski, A. P.; Tueckmantel, W. J. Org. Chem. 1991, 56, 2826-2837; (f) Craig, D.; Geach, N. J.; Pearson, Ch. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071-6098; (g) Ishikara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049-3050; (h) Ainsworth, P. J.; Craig, D.; White, A. J. P.; Williams, D. J. Tetrahedron 1996, 52, 8937-8946; (i) Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 61, 7597-7599; (j) Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438-7451; (k) Diedrich, M. K.; Klaerner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212-6218; (l) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, Th.; Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594; (m) Fukunaga, K.; Kunieda, T. Tetrahedron Lett. 1999, 40, 6041-6044; (n) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659-2662; (o) Enholm, E. J.; Jiang, Sh. J. Org. Chem. 2000, 65, 4756-4758; (p) Hayashi, H. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen K. A., Eds.; Wiley-VCH: New York, 2002; pp. 5-55.
18. Jarosz S. Tetrahedron. 53:1997;10765-10774.
19. Jarosz S., Kozłowska E., Jezewski A. Tetrahedron. 53:1997;10775-10782.
20. Jarosz S., Skóra S. Tetrahedron: Asymmetry. 11:2000;1425-1432.
21. Jarosz, S.; Szewczyk, K.; Zawisza, A. Tetrahedron: Asymmetry, next paper.
22. 2.