The preparation of resin-bound nitroalkenes and some applications in high pressure promoted cycloadditions

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 515-519

  Kuster, George J ^a   Scheeren, Hans W ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

High pressure promoted cycloadditions; Microwave heating; Nitroalkenes; Solid phase synthesis

Indexed keywords

ALKENE; NITROALKENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; SOLID PHASE EXTRACTION; STEREOCHEMISTRY; TANDEM REPEAT;

EID: 0034700858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02108-5     Document Type: Article

References (32)

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7. 2 (310 mL) and dried for at least 2 h at 70°C in vacuum (1 mm Hg). The use of DCC is not recommended because of the problematic removal of the (poorly soluble) DCU side product from the resin.
8. 2 (3x10 mL) and dried for at least 2 h at 70°C in vacuum (1 mm Hg).
9. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
10. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
11. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
12. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
13. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
14. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
15. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
16. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
17. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
18. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
19. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
20. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
21. For solid phase Diels-Alder reactions, see: (a) Gaviña, F.; Gil, P.; Palazón, B. Tetrahedron Lett. 1979, 15, 1333-1336. (b) Yedida, V.; Leznoff, C. Can. J. Chem. 1980, 58, 1144-1150. © Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136. (d) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043-1044. (e) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024. (f) Crawshaw, M.; Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. (g) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935-4938. (h) Wendeborn, S.; Mesmeaker, A. D.; Brill, W. K.-D. Synlett 1998, 865-868. (i) Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288. (j) Chen, C.; Munoz, B. Tetrahedron Lett. 1999, 40, 3491-3494. (k) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383. (l) Sparey, T. J.; Harrison, T. Tetrahedron Lett. 1998, 39, 5873-5874. (m) Winkler, J. D.; Kwak, Y. S. J. Org. Chem. 1998, 63, 8634-8635.
22. 2 (3×10 mL). The resin was dried at 70°C under reduced pressure for at least 2 h. The increase in weight of the resin was a measure of the amount of cycloadduct formed on the resin. The use of high pressure was prefered over refluxing in toluene in view of shorter reaction times and higher yields. 4-Methoxybenzyl (E/Z)-2-nitro-3-phenyl-2-propenoate reacted with 2,3-dimethylbutadiene in refluxing toluene for 48 h yielding 73% of cycloadduct; at 15 kbar and room temperature (18 h) the yield was 91%.
23. 1H NMR and mass spectroscopy. The overall yield starting from the Wang resin was 41%.
24. Zimmerman, H. E.; Nevins, T. E. J. Am. Chem. Soc. 1957, 79, 6559-6561.
25. 4 reduction is described by: Reinheckel, H.; Jahnke, D.; Tauber, G. Monath. Chem. 1969, 100, 1881-1891.
26. The cis-relationship between the amide and phenyl substituents on the cyclohexene ring agrees with the corresponding coupling constants between the adjacent protons (2.5 Hz in cis-7 and 10.5 Hz in trans-7). Compare: Serrano, J. A.; Cáceres, L. E.; Roman, E. J. Chem. Soc., Perkin. Trans. 1 1995, 1863-1871.
27. 3:MeOH=10:1 with 1% AcOH) the amino alcohol 9 was isolated as a mixture of two diastereomers in 25% overall yield from resin coupling of 1.
28. Uittenboogaard, R. M.; Seerden, J.-P. G.; Scheeren, H. W. Tetrahedron 1997, 34, 11929-11936.
29. Kuster, G. J.; Scheeren, H. W. Tetrahedron Lett. 1998, 39, 3613-3616.
30. 2 as the solvent. The reaction was performed at a pressure of 15 kbar for 20 h at 50°C. See Ref.10.
31. 1H NMR and mass spectroscopy.
32. 3) Characteristics of product 13a-e; acetal proton (EtOCHRONO) 4.89-5.10 ppm; benzylic proton (ONOCHRPh) 5.72-5.88 ppm. Mass analysis characteristics of products 13a-e; 13a HRMS (rel. int.) m/e: 356 (M+1, 0.05), 309 (-HOEt, 2.24), 279 (97.8); 13b HRMS (rel. int.) m/e: 357 (M+1, 0.00), 310 (-HOEt, 2.13), 280 (24.2); 13c HRMS (rel. int.) m/e: 345 (M+1, 0.00), 298 (-HOEt, 2.37), 268 (13.1); 13d HRMS (rel. int.) m/e: 346 (M+1, 11.5), 299 (-HOEt, 36.7), 269 (55.1); 13e HRMS (rel.int) m/e: 322 (M+1, 1.59), 275 (-HOEt, 21.7), 245 (56.0).