Direct Vinylogous Mannich-Type Reactions via Ring Opening and Rearrangement of Vinyloxiranes

Organic Letters

Volumn 6, Issue 3, 2004, Pages 345-347

  Lautens, Mark ^a   Tayama, Eiji ^a   Nguyen, Duy ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; ESTER DERIVATIVE; PIPECOLIC ACID; VINYL DERIVATIVE;

ARTICLE; HYDROGENATION; MANNICH REACTION; RING OPENING; SYNTHESIS;

EID: 1342285526     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036153j     Document Type: Article

References (28)

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2. For reviews of Lewis acid catalyzed rearrangement of epoxides, see: (a) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3; Chapter 3.3, p 733. (b) Parker, E. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. (c) Fujioka, H.; Yoshida, Y.; Kita, Y. Yuki Gosei Kagaku Kyokaishi 2003, 61, 133.
3. For reviews of Lewis acid catalyzed rearrangement of epoxides, see: (a) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3; Chapter 3.3, p 733. (b) Parker, E. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. (c) Fujioka, H.; Yoshida, Y.; Kita, Y. Yuki Gosei Kagaku Kyokaishi 2003, 61, 133.
4. For recent examples of Lewis acid catalyzed rearrangement of vinyloxirane, see: (a) Jung, M. E.; Anderson, K. L. Tetrahedron Lett. 1997, 38, 2605. (b) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. (c) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 825.
5. For recent examples of Lewis acid catalyzed rearrangement of vinyloxirane, see: (a) Jung, M. E.; Anderson, K. L. Tetrahedron Lett. 1997, 38, 2605. (b) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. (c) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 825.
6. For recent examples of Lewis acid catalyzed rearrangement of vinyloxirane, see: (a) Jung, M. E.; Anderson, K. L. Tetrahedron Lett. 1997, 38, 2605. (b) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. (c) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 825.
7. For recent examples of transition-metal-catalyzed rearrangement of vinyloxirane: (a) Courillon, C.; Fol, R. F.; Vandendris, E. Malacria, M. Tetrahedron Lett. 1997, 38, 5493. (b) Bideau, F. L.; Gilloir, F.; Nilsson, Y.; Aubert, C., Malacria, M. Tetrahedron 1996, 52, 7487.
8. For recent examples of transition-metal-catalyzed rearrangement of vinyloxirane: (a) Courillon, C.; Fol, R. F.; Vandendris, E. Malacria, M. Tetrahedron Lett. 1997, 38, 5493. (b) Bideau, F. L.; Gilloir, F.; Nilsson, Y.; Aubert, C., Malacria, M. Tetrahedron 1996, 52, 7487.
9. For application of β,γ-unsaturated aldehydes in organic synthesis: (a) Hughes, G.; Lautens, M.; Wen, C. Org. Lett. 2000, 2, 107. (b) Ahmar, M.; Bloch, R.; Mandville, G.; Romain, I. Tetrahedron Lett. 1992, 33, 2501. (c) Roush, W. R. J. Org. Chem. 1991, 56, 4151.
10. For application of β,γ-unsaturated aldehydes in organic synthesis: (a) Hughes, G.; Lautens, M.; Wen, C. Org. Lett. 2000, 2, 107. (b) Ahmar, M.; Bloch, R.; Mandville, G.; Romain, I. Tetrahedron Lett. 1992, 33, 2501. (c) Roush, W. R. J. Org. Chem. 1991, 56, 4151.
11. For application of β,γ-unsaturated aldehydes in organic synthesis: (a) Hughes, G.; Lautens, M.; Wen, C. Org. Lett. 2000, 2, 107. (b) Ahmar, M.; Bloch, R.; Mandville, G.; Romain, I. Tetrahedron Lett. 1992, 33, 2501. (c) Roush, W. R. J. Org. Chem. 1991, 56, 4151.
12. (a) Lautens, M.; Maddess, M. L.; Sauer, E. L. O.; Ouellet, S. G. Org. Lett. 2002, 4, 83.
13. (b) Lautens, M.; Ouellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079.
14. For a review of vinylogous Mannich reactions, see: Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221.
15. For recent examples of a Lewis acid-catalyzed Mannich-type reaction using an α-imino ester as an electrophile: (a) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 65, 2583. (b) Kobayashi, S.; Matubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (c) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (d) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
16. For recent examples of a Lewis acid-catalyzed Mannich-type reaction using an α-imino ester as an electrophile: (a) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 65, 2583. (b) Kobayashi, S.; Matubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (c) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (d) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
17. For recent examples of a Lewis acid-catalyzed Mannich-type reaction using an α-imino ester as an electrophile: (a) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 65, 2583. (b) Kobayashi, S.; Matubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (c) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (d) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
18. For recent examples of a Lewis acid-catalyzed Mannich-type reaction using an α-imino ester as an electrophile: (a) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 65, 2583. (b) Kobayashi, S.; Matubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (c) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (d) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
19. For recent examples of a Lewis acid-catalyzed Mannich-type reaction using an α-imino ester as an electrophile: (a) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 65, 2583. (b) Kobayashi, S.; Matubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (c) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (d) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
20. Examples of direct Mannich-type reaction to an α-imino ester: (a) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (b) Córdova, A.; Notz, Wolfgang.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (c) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995.
21. Examples of direct Mannich-type reaction to an α-imino ester: (a) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (b) Córdova, A.; Notz, Wolfgang.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (c) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995.
22. Examples of direct Mannich-type reaction to an α-imino ester: (a) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. (b) Córdova, A.; Notz, Wolfgang.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (c) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995.
23. In the case of an α,β-or β,γ-unsaturated aldehyde as the nucleophilic reagent under the same conditions: trans-2-methyl-2-butenal, 0% yield; 2-methyl-3-butenal, 67% yield. These facts indicate that a β,γ-unsaturated aldehyde has to be used for the direct vinylogous Mannich-type reaction. 2-Methyl-3-butenal was prepared by the following literature using crotyl bromide instead of allyl bromide: Crimmins, M. T.; Kirincich, S. J.; Wells, A. J.; Choy, A. L. Synth. Commun. 1998, 28, 3675. Spectroscopic data: see the Supporting Information.
24. The configuration was determined according to the following literature procedure: Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. See the Supporting Information.
25. 13C NMR spectroscopy based on the shift of the 5-Me substituent. See the Supporting Information.
26. Enantio-and/or diastereoselective synthesis of 5-substituted pipecolinic acid derivatives: (a) Cellier, M.; Mialhe, Y. G.; Husson, H. P.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 2000, 11, 3913. (b) Barluenga, J.; Aznar, F. ; Valdés, C.; Ribas, C. J. Org. Chem. 1998, 63, 3918.
27. Enantio-and/or diastereoselective synthesis of 5-substituted pipecolinic acid derivatives: (a) Cellier, M.; Mialhe, Y. G.; Husson, H. P.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 2000, 11, 3913. (b) Barluenga, J.; Aznar, F. ; Valdés, C.; Ribas, C. J. Org. Chem. 1998, 63, 3918.
28. 2 atmosphere in AcOH to yield 9 in 35% yield with excellent diastereoselectivity. It is expected that the reaction proceeded via the same intermediate as 3a. On the basis of the result, the configurations of 8 and 9 were also determined. See the Supporting Information.