Stereoselectivity in Diels-Alder reactions of diene-substituted N-alkoxycarbonyl-1,2-dihydropyridines

Journal of Organic Chemistry

Volumn 72, Issue 9, 2007, Pages 3458-3466

  Krow, Grant R ^a   Huang, Qiuli ^a   Szczepanski, Steven W ^a   Hausheer, Fredrick H ^b   Carroll, Patrick J ^c  

^a Temple University   (United States)

^b BioNumerik Pharmaceuticals Inc   (United States)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTIONS; DIENES; ENDO PHENYL ISOMERS; METHYL VINYL KETONE (MVK);

ISOMERS; KETONES; REACTION KINETICS; REGIOSELECTIVITY; STEREOSELECTIVITY; STYRENE; SUBSTITUTION REACTIONS;

PYRIDINE;

ALKADIENE; ALKYL GROUP; CARBONYL DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; KETONE DERIVATIVE; METHYLVINYL KETONE; STYRENE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; ENTROPY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

BUTANONES; CHEMISTRY, ORGANIC; HYDROCARBONS, CYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM; STYRENES;

EID: 34247631517     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0700575     Document Type: Article

References (45)

1. (a) Weinstein, B.; Lin, L. C.; Fowler, F. W. J. Org. Chem. 1980, 45, 1657-1661.
2. (b) Fowler, F. W. J. Org. Chem. 1972, 37, 1321-1323.
3. (c) Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685-7689.
4. For reviews, see: (d) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1-42.
5. (e) Stout, D.; Meyers, A. I. Chem. Rev. 1982, 82, 223-243.
6. (f) Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141-1156.
7. Iboga alkaloids: (a) Raucher, S.; Bray, B. L. J. Org. Chem. 1985, 50, 3236-3237.
8. (b) Raucher, S.; Lawrence, R. F. Tetrahedron Lett. 1983, 24, 2927-2930.
9. (c) Sundberg, R. J.; Bloom, J. D. J. Org. Chem. 1981, 46, 4836-4842.
10. (d) Sundberg, R. J.; Cherney, R. J. J. Org. Chem. 1990, 55, 6028-6037.
11. (e) Sundberg, R. J.; Amat, M.; Fernando, A. M. J. Org. Chem. 1987, 52, 3151-3159.
12. (f) Krow, G. R.; Shaw, D. A.; Lynch, B.; Lester, W.; Szczepanski, S. W.; Raghavachari, R.; Derome, A. E. J. Org. Chem. 1988, 53, 2258-2262;
13. See also: Hodgson, D. M.; Galano, J.-M. Org. Lett. 2005, 7, 2221-2224.
14. (g) Marazano, C.; Fourrey, J. L.; Das, B. C. J. Chem. Soc., Chem. Commun. 1981, 37-39.
15. Tetrahydroisoquinoline alkaloids: (a) MaGee, D. I.; Lee, M. L. Tetrahedron Lett. 2001, 42, 7177-7180.
16. (b) MaGee, D. I.; Lee, M. L. Synlett 1997, 7, 786-788.
17. (c) Wender, P.; Schaus, J.; Torney, D. Tetrahedron Lett. 1979, 27, 2485-2488.
18. (d) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159.
19. (e) Mariano, P. S.; Dunaway-Mariano, D.; Huesmann, P. L. J. Org. Chem. 1979, 44, 124-133.
20. (f) Mariano, P. S.; Dunaway-Mariano, D.; Huesmann, P. L.; Beamer, R. L. Tetrahedron Lett. 1977, 18, 4299-4302.
21. (g) Baxter, E. W.; Labaree, D.; Chao, S.; Mariano, P. S. J. Org. Chem. 1989, 54, 2893-2904.
22. (h) Comins, D. L.; Al-war, R. S. J. Org. Chem. 1992, 57, 4098-4103.
23. (i) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229-231.
24. Homoepibatidines: Krow, G. R.; Cheung, O. H.; Hu, Z.; Huang, Q.; Hutchinson, J.; Liu, N.; Nguyen, K. T.; Ulrich, S.; Yuan, J.; Xiao, Y.; Wypij, D. M.; Zuo, F.; Carroll, P. J. Tetrahedron 1999, 55, 7747-7756.
25. Piperidines: (a) Sales, M.; Charette, A. B. Org. Lett. 2005, 7, 5773-5776.
26. (b) Arakawa, Y.; Murakami, T.; Ozawa, F.; Arakawa, Y.; Yoshifuji, S. Tetrahedron 2003, 59, 7555-7563.
27. Cyclohexanecarboxylic acids: (a) Arakawa, Y.; Tajima, M.; Arakawa, Y.; Yoshifuji, S. Chem. Pharm. Bull. 2005, 53, 81-85.
28. (b) Campbell, M. M.; Mahon, M. F.; Sainsbury, M.; Searle, P. A.; Davies, G. M. Tetrahedron Lett. 1991, 32, 951-954.
29. (c) Campbell, M. M.; Sainsbury, M.; Searle, P. A.; Davies, G. M. Tetrahedron Lett. 1992, 33, 3181-3184.
30. Bridged azapolycycles: (a) Choi, Y.; White, J. D. J. Org. Chem. 2004, 69, 3758-3764.
31. (b) Krow, G. R.; Lee, Y. B.; Raghavachari, R.; Szczepanski, S. W.; Alston, P. V. Tetrahedron 1991, 47, 8499-8154.
32. Sundberg, R. J.; Hamilton, G.; Trindle, C. J. Org. Chem. 1986, 51, 3672-3679.
33. Krow, G. R.; Carey, J. T.; Cannon, K. C.; Henz, K. J. Tetrahedron Lett. 1982, 23, 2527-2528.
34. Equilibrium measurements for cyclohexa-1,3-diene cycloadducts show endo adducts to be favored with methyl vinyl ketone [K(exo/endo) = 0.41]: Ouellette, R. J.; Booth, G. E. J. Org. Chem. 1966, 31, 3065-3067.
35. Methyl acrylate [K(exo/endo) = 0.46]: Ouellette, R. J.; Booth, G. E. J. Org. Chem. 1965, 30, 423-425.
36. Krow, G. R.; Cannon, K. C.; Carey, J. T.; Lee, Y. B.; Szczepanski, S. W.; Ramjit, H. G. J. Heterocycl. Chem. 1985, 22, 131-135.
37. Krow, G. R.; Alston, P. V.; Szczepanski, S. W.; Raghavachari, R.; Cannon, K. C.; Carey, J. T. Synth. Commun. 1990, 20, 1949-1958.
38. Acrylonitrile adds to N-methoxycarbonyl-4-hydroxyethyl-1,2- dihydropyridine or its 3-methyl-4-hydroxyethyl counterpart to give 2.1:1 and 1.8:1 mixtures of exo/endo cycloadducts. The same substrates with methyl acrylate, acrolein, or methyl vinyl ketone gave mixtures described as ranging from 1:2 to 1:1 exo/endo cycloadducts without further experimental detail; see ref 3a.
39. Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 615-618.
40. Kurita, J.; Iwata, K.; Sakai, H.; Takashi, T. Chem. Pharm. Bull. 1985, 33, 4572-4580.
41. (a) Krow, G. R.; Rodenbaugh, R. Org. Magn. Reson. 1973, 5, 73-75.
42. (b) Krow, G. R.; Rodenbaugh, R.; Carmosin, R.; Figures, W.; Pannella, H.; Devicaris, G.; Grippi, M. J. Am. Chem. Soc. 1973, 95, 5273-5280.
43. (a) Photochemical: Mlcoch, J.; Steckhan, E. Angew. Chem. 1985, 97, 429-431.
44. (b) Electrochemical: Mlcoch, J.; Steckhan, E. Tetrahedron Lett. 1987, 28, 1081-1084.
45. Garcia, J. I.; Mayoral, J. A.; Salvatella, L. Acc. Chem. Res. 2000, 33, 658-664.