Tetronamides as latent acyclic vinylogous amides in formal Aza-[3 + 3] cycloaddition reactions with α,β-unsaturated iminium salts. An unexpected rearrangement and an approach to synthesis of substituted piperidines

Journal of Organic Chemistry

Volumn 69, Issue 20, 2004, Pages 6732-6738

  Sydorenko, Nadiya ^a   Hsung, Richard P ^a   Darwish, Ossama Saleh ^a   Hahn, Juliet M ^a,b   Liu, Jia ^a  

^a University of Minnesota   (United States)

^b ARKANSAS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC VINYLOGOUS AMIDES; REACTION TEMPERATURES; REGIOISOMERIC CYCLOADDUCTS; TETROAMIDES;

ISOMERS; REACTION KINETICS; SALTS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

NITROGEN COMPOUNDS;

AMIDE; DIHYDROPYRIDINE; HETEROCYCLIC COMPOUND; LACTONE; PIPERIDINE; TETRONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; RING OPENING; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

AMIDES; IMINES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM;

EID: 4644248178     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049108d     Document Type: Article

References (68)

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14. The term "formal [3 + 3]" was used to describe [3 + 3] carbocycloadditions. See: (a) Seebach, D.; Missbach, M.; Calderari, G.; Eberle, M. J. Am. Chem. Soc. 1990, 112, 7625. For earlier studies on [3 + 3] carbo-cycloadditions, see: (b) Landesman, H. K.; Stork, G. J. Am. Chem. Soc. 1956, 78, 5129.
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21. For recent studies in this area, see: (a) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286. (c) Chang, M.-Y.; Lin, J. Y.-C.; Chen, S. T.; Chang, N.-C. J. Chin. Chem. Soc. 2002, 49, 1079. (d) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596. (e) Davies, I. W.; Marcoux, J.-F.; Reider, P. J. Org. Lett. 2001, 3, 209. (f) Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251. (g) Nemes, P.; Balázs, B.; Toth, G.; Scheiber, P. Synlett 1999, 222. (h) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann,-J.-P. Acta Crystallogr. 1999, C55, 1698. (i) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (j) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (k) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215 and 6677. (l) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1992, 57, 5319.
22. For recent studies in this area, see: (a) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286. (c) Chang, M.-Y.; Lin, J. Y.-C.; Chen, S. T.; Chang, N.-C. J. Chin. Chem. Soc. 2002, 49, 1079. (d) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596. (e) Davies, I. W.; Marcoux, J.-F.; Reider, P. J. Org. Lett. 2001, 3, 209. (f) Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251. (g) Nemes, P.; Balázs, B.; Toth, G.; Scheiber, P. Synlett 1999, 222. (h) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann,-J.-P. Acta Crystallogr. 1999, C55, 1698. (i) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (j) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (k) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215 and 6677. (l) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1992, 57, 5319.
23. For recent studies in this area, see: (a) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286. (c) Chang, M.-Y.; Lin, J. Y.-C.; Chen, S. T.; Chang, N.-C. J. Chin. Chem. Soc. 2002, 49, 1079. (d) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596. (e) Davies, I. W.; Marcoux, J.-F.; Reider, P. J. Org. Lett. 2001, 3, 209. (f) Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251. (g) Nemes, P.; Balázs, B.; Toth, G.; Scheiber, P. Synlett 1999, 222. (h) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann,-J.-P. Acta Crystallogr. 1999, C55, 1698. (i) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (j) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (k) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215 and 6677. (l) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1992, 57, 5319.
24. For recent studies in this area, see: (a) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286. (c) Chang, M.-Y.; Lin, J. Y.-C.; Chen, S. T.; Chang, N.-C. J. Chin. Chem. Soc. 2002, 49, 1079. (d) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596. (e) Davies, I. W.; Marcoux, J.-F.; Reider, P. J. Org. Lett. 2001, 3, 209. (f) Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251. (g) Nemes, P.; Balázs, B.; Toth, G.; Scheiber, P. Synlett 1999, 222. (h) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann,-J.-P. Acta Crystallogr. 1999, C55, 1698. (i) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (j) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (k) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215 and 6677. (l) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1992, 57, 5319.
25. For recent studies in this area, see: (a) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286. (c) Chang, M.-Y.; Lin, J. Y.-C.; Chen, S. T.; Chang, N.-C. J. Chin. Chem. Soc. 2002, 49, 1079. (d) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596. (e) Davies, I. W.; Marcoux, J.-F.; Reider, P. J. Org. Lett. 2001, 3, 209. (f) Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251. (g) Nemes, P.; Balázs, B.; Toth, G.; Scheiber, P. Synlett 1999, 222. (h) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann,-J.-P. Acta Crystallogr. 1999, C55, 1698. (i) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (j) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (k) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215 and 6677. (l) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1992, 57, 5319.
26. For recent studies in this area, see: (a) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286. (c) Chang, M.-Y.; Lin, J. Y.-C.; Chen, S. T.; Chang, N.-C. J. Chin. Chem. Soc. 2002, 49, 1079. (d) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596. (e) Davies, I. W.; Marcoux, J.-F.; Reider, P. J. Org. Lett. 2001, 3, 209. (f) Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251. (g) Nemes, P.; Balázs, B.; Toth, G.; Scheiber, P. Synlett 1999, 222. (h) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann,-J.-P. Acta Crystallogr. 1999, C55, 1698. (i) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (j) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (k) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215 and 6677. (l) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1992, 57, 5319.
27. For recent studies in this area, see: (a) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286. (c) Chang, M.-Y.; Lin, J. Y.-C.; Chen, S. T.; Chang, N.-C. J. Chin. Chem. Soc. 2002, 49, 1079. (d) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596. (e) Davies, I. W.; Marcoux, J.-F.; Reider, P. J. Org. Lett. 2001, 3, 209. (f) Davies, I. W.; Taylor, M.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251. (g) Nemes, P.; Balázs, B.; Toth, G.; Scheiber, P. Synlett 1999, 222. (h) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann,-J.-P. Acta Crystallogr. 1999, C55, 1698. (i) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (j) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (k) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215 and 6677. (l) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1992, 57, 5319.
28. For intermolecular formal aza-[3 + 3] cycloadditions, see: (a) Sklenicka, H. M.; Hsung, R. P.; McLaughlin, M. J.; Wei, L.-L.; Gerasyuto, A. I.; Brennessel, W. W. J. Am. Chem. Soc. 2002, 124, 10435. (b) Sklenicka, H. M.; Hsung, R. P.; Wei, L.-L.; McLaughlin, M. J.; Gerasyuto, A. I.; Degen, S. J.; Mulder, J. A. Org. Lett. 2000, 2, 1161. (c) Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Douglas, C. J.; McLaughlin, M. J.; Mulder, J. A.; Yao, L. J. Org. Lett. 1999, 1, 509.
29. For intermolecular formal aza-[3 + 3] cycloadditions, see: (a) Sklenicka, H. M.; Hsung, R. P.; McLaughlin, M. J.; Wei, L.-L.; Gerasyuto, A. I.; Brennessel, W. W. J. Am. Chem. Soc. 2002, 124, 10435. (b) Sklenicka, H. M.; Hsung, R. P.; Wei, L.-L.; McLaughlin, M. J.; Gerasyuto, A. I.; Degen, S. J.; Mulder, J. A. Org. Lett. 2000, 2, 1161. (c) Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Douglas, C. J.; McLaughlin, M. J.; Mulder, J. A.; Yao, L. J. Org. Lett. 1999, 1, 509.
30. For intermolecular formal aza-[3 + 3] cycloadditions, see: (a) Sklenicka, H. M.; Hsung, R. P.; McLaughlin, M. J.; Wei, L.-L.; Gerasyuto, A. I.; Brennessel, W. W. J. Am. Chem. Soc. 2002, 124, 10435. (b) Sklenicka, H. M.; Hsung, R. P.; Wei, L.-L.; McLaughlin, M. J.; Gerasyuto, A. I.; Degen, S. J.; Mulder, J. A. Org. Lett. 2000, 2, 1161. (c) Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Douglas, C. J.; McLaughlin, M. J.; Mulder, J. A.; Yao, L. J. Org. Lett. 1999, 1, 509.
31. For intramolecular formal aza-[3 + 3] cycloaddition, see: Wei, L.-L.; Sklenicka, H. M.; Gerasyuto, A. I.; Hsung, R. P. Angew. Chem., Int. Ed. 2001, 40, 1516.
32. For our applications in natural product syntheses, see: (a) Luo, S.; Zificsak, C. Z.; Hsung, R. P. Org. Lett. 2003, 5, 4709. (b) McLaughlin, M. J.; Hsung, R. P.; Cole, K. C.; Hahn, J. M.; Wang, J. Org. Lett. 2002, 4, 2017.
33. For our applications in natural product syntheses, see: (a) Luo, S.; Zificsak, C. Z.; Hsung, R. P. Org. Lett. 2003, 5, 4709. (b) McLaughlin, M. J.; Hsung, R. P.; Cole, K. C.; Hahn, J. M.; Wang, J. Org. Lett. 2002, 4, 2017.
34. The advantage of using α,β-unsaturated iminium salts in regiochemical control has also recently been noted; see: Cravotto, G.; Nano, G. M.; Tagliapietra, S. Synthesis 2001, 49.
35. Hickmott, P. W.; Sheppard, G. J. Chem. Soc. C 1971, 2112.
36. (a) Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493.
37. (b) Paulvannan,; K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 6677.
38. (c) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215.
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40. (a) Greenhill, J. V.; Mohamed, M. J. Chem. Soc., Perkin Trans. 1 1979, 1411.
41. (b) Chaaban, J.; Greenhill, J. V.; Rauli, M. J. Chem. Soc., Perkin Trans. 1 1981, 3120.
42. For leading references on electrocyclic ring-closures involving 1-azatrienes, see: (a) Maynard, D. F.; Okamura, W. H. J. Org. Chem. 1995, 60, 1763. (b) de Lera, A. R.; Reischl, W.; Okamura, W. H. J. Am. Chem. Soc. 1989, 111, 4051. For an earlier account, see: (c) Oppolzer, V. W. Angew. Chem. 1972, 22, 1108.
43. For leading references on electrocyclic ring-closures involving 1-azatrienes, see: (a) Maynard, D. F.; Okamura, W. H. J. Org. Chem. 1995, 60, 1763. (b) de Lera, A. R.; Reischl, W.; Okamura, W. H. J. Am. Chem. Soc. 1989, 111, 4051. For an earlier account, see: (c) Oppolzer, V. W. Angew. Chem. 1972, 22, 1108.
44. For leading references on electrocyclic ring-closures involving 1-azatrienes, see: (a) Maynard, D. F.; Okamura, W. H. J. Org. Chem 1995, 60, 1763. (b) de Lera, A. R.; Reischl, W.; Okamura, W. H. J. Am. Chem. Soc. 1989, 111, 4051. For an earlier account, see: (c) Oppolzer, V. W. Angew. Chem. 1972, 22, 1108.
45. For recent elegant accounts on stereoselective ring-closure of 1-azatrienes, see: (a) Tanaka, K.; Katsumura, S. J. Am. Chem. Soc. 2002, 124, 9660. (b) Tanaka, K.; Mori, H.; Yamamoto, M.; Katsumura, S. J. Org. Chem. 2001, 66, 3099.
46. For recent elegant accounts on stereoselective ring-closure of 1-azatrienes, see: (a) Tanaka, K.; Katsumura, S. J. Am. Chem. Soc. 2002, 124, 9660. (b) Tanaka, K.; Mori, H.; Yamamoto, M.; Katsumura, S. J. Org. Chem. 2001, 66, 3099.
47. For a review on rotational preferences leading to diastereomeric induction during a 6π-electron electrocyclic ring closure, see: Okamura, W. H.; de Lera, A. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Paquette, L. A., Volume Ed.; Pergamon Press: 1991, Vol. 5, pp 699-750.
48. For other studies involving 1-heterotrienes in formation of a single-ring system, see: (a) Moorhoff, C. M. Synthesis 1997, 685. (c) Jonassohn, M.; Sterner, O.; Anke, H. Tetrahedron 1998, 52, 1473. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. Bull. 1995, 44, 2118.
49. For other studies involving 1-heterotrienes in formation of a single-ring system, see: (a) Moorhoff, C. M. Synthesis 1997, 685. (c) Jonassohn, M.; Sterner, O.; Anke, H. Tetrahedron 1998, 52, 1473. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. Bull. 1995, 44, 2118.
50. For other studies involving 1-heterotrienes in formation of a single-ring system, see: (a) Moorhoff, C. M. Synthesis 1997, 685. (c) Jonassohn, M.; Sterner, O.; Anke, H. Tetrahedron 1998, 52, 1473. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. Bull. 1995, 44, 2118.
51. For a recent review on preparations of piperidines, see: Laschat, S.; Dickner, T. Synthesis 2000, 1781.
52. For recent approaches to dihydropyridines and related piperidines, see: (a) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. (c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (d) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685. (e) Comins, D. L.; Zhang, Y.; Joseph, S. P. Org. Lett. 1999, 1, 657. (f) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651. (h) References 15 and 13b-e.
53. For recent approaches to dihydropyridines and related piperidines, see: (a) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. (c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (d) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685. (e) Comins, D. L.; Zhang, Y.; Joseph, S. P. Org. Lett. 1999, 1, 657. (f) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651. (h) References 15 and 13b-e.
54. For recent approaches to dihydropyridines and related piperidines, see: (a) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. (c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (d) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685. (e) Comins, D. L.; Zhang, Y.; Joseph, S. P. Org. Lett. 1999, 1, 657. (f) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651. (h) References 15 and 13b-e.
55. For recent approaches to dihydropyridines and related piperidines, see: (a) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. (c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (d) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685. (e) Comins, D. L.; Zhang, Y.; Joseph, S. P. Org. Lett. 1999, 1, 657. (f) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651. (h) References 15 and 13b-e.
56. For recent approaches to dihydropyridines and related piperidines, see: (a) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. (c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (d) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685. (e) Comins, D. L.; Zhang, Y.; Joseph, S. P. Org. Lett. 1999, 1, 657. (f) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651. (h) References 15 and 13b-e.
57. For recent approaches to dihydropyridines and related piperidines, see: (a) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. (c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (d) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685. (e) Comins, D. L.; Zhang, Y.; Joseph, S. P. Org. Lett. 1999, 1, 657. (f) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651. (h) References 15 and 13b-e.
58. For recent approaches to dihydropyridines and related piperidines, see: (a) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. (c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (d) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685. (e) Comins, D. L.; Zhang, Y.; Joseph, S. P. Org. Lett. 1999, 1, 657. (f) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651. (h) References 15 and 13b-e.
59. For recent approaches to dihydropyridines and related piperidines, see: (a) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. (c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (d) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685. (e) Comins, D. L.; Zhang, Y.; Joseph, S. P. Org. Lett. 1999, 1, 657. (f) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651. (h) References 15 and 13b-e.
60. The head-to-head regiochemistry resulting from formal aza-[3 + 3] cycloadditions of these tetronamides was also unambiguously assigned using the X-ray structure of the hydrogenated cycloadduct 16. Please see Supporting Information for the X-ray information.
61. Shen, H. C.; Wang, J.; Cole, K. P.; McLaughlin, M. J.; Morgan, C. D.; Douglas, C. J.; Hsung, R. P.; Coverdale, H. A.; Gerasyuto, A. I.; Hahn, J. M.; Liu, J.; Wei, L.-L.; Sklenicka, H. M.; Zehnder, L. R.; Zificsak, C. A. J. Org. Chem. 2003, 68, 1729.
62. For some examples involving torquoselective processes, see: (a) Giese, S.; Kastrup, L.; Stiens, D.; West, F. G. Angew. Chem., Int. Ed. 2000, 39, 1970. (b) Hsung, R. P.; Quinn, J. F.; Weisenberg, B. A.; Wulff, W. D. Yap, G. P. A.; Rheingold, A. L. J. Chem. Soc., Chem. Comm. 1997, 615.
63. For some examples involving torquoselective processes, see: (a) Giese, S.; Kastrup, L.; Stiens, D.; West, F. G. Angew. Chem., Int. Ed. 2000, 39, 1970. (b) Hsung, R. P.; Quinn, J. F.; Weisenberg, B. A.; Wulff, W. D. Yap, G. P. A.; Rheingold, A. L. J. Chem. Soc., Chem. Comm. 1997, 615.
64. Synthesis of 44: Ireland, R. E.; Thompson, W. J. J. Org. Chem. 1979, 44, 3041.
65. Debenzylated product 51 was also occasionally isolated in 16% yield.
66. (a) Akhrem, A. A.; Lakhvich, F. A.; Lis, L. G.; Pshenichnyi, V. N.; Arsen'ev, A. S. Zh. Org. Khim. 1980, 16, 1290.
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