Highly selective Diels-Alder reactions of directly connected enyne dienophiles

Journal of the American Chemical Society

Volumn 129, Issue 3, 2007, Pages 645-657

  Dai, Mingji ^a   Sarlah, David ^a   Yu, Maolin ^a   Danishefsky, Samuel J ^a,b   Jones, Gavin O ^c   Houk, K N ^c  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ADDITION REACTIONS; AROMATIZATION; ESTERS; MOLECULAR STRUCTURE; REACTION KINETICS;

CYCLOADDITION; DIELS ALDER REACTIONS; DIENOPHILES; ENYNES;

UNSATURATED COMPOUNDS;

ACETYLENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; STEREOCHEMISTRY;

ACETYLENE; ALGORITHMS; ALKADIENES; CATALYSIS; CYCLIZATION; ESTERS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL;

EID: 33846433155     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065762u     Document Type: Article

References (64)

1. (a) Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98.
2. (b) Alder, K.; Rickert, H. F. Justus Liebigs Ann. Chem. 1936, 524, 180.
3. (a) Danishefsky, S. J.; Singh, R. K.; Gammill, R. B. J. Org. Chem. 1978, 43, 379.
4. (b) Danishefsky, S. J.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716.
5. (a) Yang, Z.-Q.; Danishefsky, S. J. J. Am. Chem. Soc. 2003, 125, 9602.
6. (b) Geng, X.; Danishefsky, S. J. Org. Lett. 2004, 6, 413.
7. (c) Yang, Z.-Q.; Geng, X.; Solit, D.; Pratilas, C. A.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 7881.
8. (d) Geng, X.; Yang, Z.-Q.; Danishefsky, S. J. Synlett 2004, 1325.
9. Yoshino, T.; Ng, F.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 14185.
10. (a) Kocieński, P. J.; Street, S. D. A.; Yeates, C.; Campbell, S. F. J. Chem. Soc., Perkin Trans. 1 1987, 2171.
11. (b) Barluenga, J.; Aznar, F.; Barluenga, S.; Fernández, M.; Martín, A.; García-Granda, S.; Piñera-Nicolás, A. Chem.-Eur. J. 1998, 4, 2280-2298.
12. (c) Barluenga, J.; Fernández-Rodríguez, M. A.; Aguilar, E. Org. Lett. 2002, 4, 3659.
13. (a) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 315.
14. (b) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668.
15. (c) Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779.
16. (a) Sauer, J.; Mielert, A.; Wiest, H. Chem. Ber. 1964, 3183.
17. (b) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16.
18. (a) Konovalov, A. I.; Samuilov, Ya. D.; Slepova, L. F.; Breus, V. A. Zh. Org. Khim. 1973, 9, 2519.
19. (b) Samuilov, Ya. D.; Nurullina, R. L.; Konovalov, A. I. Zh. Org. Khim. 1981, 17, 1494.
20. (c) Samuilov, Ya. D.; Nurullina, R. L.; Konovalov, A. I. Zh. Org. Khim. 1982, 18, 2253.
21. (d) Samuilov, Ya. D.; Nurullina, R. L.; Konovalov, A. I. Zh. Org. Khim. 1983, 19, 1431.
22. Froese, R. D. J.; Coxon, J. M.; West, S. C.; Morokuma, K. J. Org. Chem. 1997, 62, 6991.
23. Singleton, D. A.; Schulmeier, B. E.; Hang, C.; Thomas, A. A.; Leung, S.-W.; Merrigan, S. R. Tetrahedron 2001, 57, 5149.
24. (a) Fuks, R.; Viehe, H. G. In Chemistry of Acetylenes: Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; p 478.
25. (b) Veliev, M. G.; Guseinov, M. M.; Yanovskaya, L. A.; Burstein, K. Y. Tetrahedron Lett. 1985, 41, 749.
26. (c) Bondarev, G. N.; Ryzhov, V. A.; Chelpanova, L. F.; Petrov, A. A. Zh. Org. Khim. 1967, 3, 816.
27. (a) Sustmann, R. Tetrahedron Lett. 1971, 29, 2721.
28. (b) Sustmann, R.; Schubert, R. Angew. Chem., Int. Ed. Engl. 1972, 11, 840.
29. (c) Sustmann, R. Pure Appl. Chem. 1974, 40, 569.
30. (d) Houk, K. N. Acc. Chem. Res. 1975, 8, 361.
31. (e) Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092.
32. (a) Alston, P. V.; Ottenbrite, R. M.; Shillady, D. D. J. Org. Chem. 1973, 38, 4075.
33. (b) Alston, P. V.; Ottenbrite, R. M. J. Org. Chem. 1975, 40, 1111.
34. (c) Alston, P. V.; Ottenbrite, R. M.; Cohen, T. J. Org. Chem. 1978, 43, 1864.
35. (d) Cohen, T.; Ruffner, R. J.; Shull, D. W.; Daniewski, W. M.; Ottenbrite, R. M.; Alston, P. V. J. Org. Chem. 1978, 43, 4052. For a review. see
36. (e) Ginsburg, D. Tetrahedron 1983, 39, 2095.
37. Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381.
38. (a) Jones, G. O.; Ess, D. H.; Houk, K. N. Helv. Chim. Acta 2005, 88, 1702.
39. (b) Jones, G. O.; Robbins, J. A.; Theofanis, P. L.; Dai, M. J.; Houk, K. N.; Danishefsky, S. J., manuscript in preparation.
40. Strozier, R. W.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1979, 101, 1340.
41. Houk, K. N.; Munchausen, L. L. J. Am. Chem. Soc. 1976, 98, 937.
42. Ussing, B. R.; Hang, C.; Singleton, D. A. J. Am Chem. Soc. 2006, 128, 7594.
43. (a) Wenkert, E.; Leicht, C. L.; Adams, K. A. H. Can. J. Chem. 1963, 41, 1844.
44. (b) Ramachandran, P. V.; Rudd, M. T.; Reddy, M. V. R. Tetrahedron Lett. 2005, 46, 2547.
45. Rubottom, G. M.; Krueger, D. S. Tetrahedron Lett. 1977, 18, 611 and references therein.
46. Krägeloh, K.; Simchen, G.; Schweiker, K. Liebigs Ann. Chem. 1985, 2352.
47. Rubottom, G. M.; Gruber, J. M. J. Org. Chem. 1978, 43, 1599.
48. (a) Negishi, E.-I.; Van, Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639.
49. (b) Negishi, E.-I.; Qian, M.; Zeng, F.; Anasiasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597.
50. Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215.
51. Liang, J. J.; Foote, C. S. Tetrahedron Lett. 1982, 23, 3039.
52. (a) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252.
53. (b) Kozmin, S. A.; Green, M. T.; Rawal, V. H. J. Org. Chem. 1999, 64, 8045.
54. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
55. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
56. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
57. (a) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
58. (b) Stephens, P. J.; Devlin, F. J.; Ashvar, C. S.; Bak, K. L.; Taylor, P. R.; Frisch, M. J. ACS Symp. Ser. 1996, 629, 105.
59. (c) Hehre, W. J.; Radom, L.; Schleyer, P. V.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
60. Frisch, M. J., et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
61. 2 = 0) shown below, corresponding to the adduct formed from nucleophilic addition of the diene. The energy of this intermediate is 12.5 kcal/mol, which is 1.5 kcal/mol lower than the transition state. However, the ring-closing transition structure proceeding from this intermediate could not be found, most likely because of the near-zero activation barrier for conversion of this zwitterions to product. (Diagram presented)
62. (a) Domingo, L. R.; Jones, R. A.; Picher, M. T.; Sepúlveda-Arque. s, J. Tetrahedron 1995, 51, 8739.
63. (b) Domingo, L. R.; Arnó, M.; Andrés, J. Tetrahedron Lett. 1996, 37, 7573.
64. (c) Domingo, L. R.; Picher, M. T.; Aurell, M. J. J. Phys. Chem. A 1999, 103, 11425.