Diastereoselectivity of enolate anion protonation. H/D exchange of β-substituted ethyl butanoates in ethanol-d

Journal of the American Chemical Society

Volumn 119, Issue 3, 1997, Pages 479-486

  Mohrig, Jerry R ^a   Rosenberg, Robert E ^a,b   Apostol, John W ^a   Bastienaansen, Mark ^a   Evans, Jordan W ^a   Franklin, Sonya J ^a   Frisbie, C Daniel ^a   Fu, Sabrina S ^a   Hamm, Michelle L ^a   Hirose, Christopher B ^a   Hunstad, David A ^a   James, Thomas L ^a   King, Randall W ^a   Larson, Christopher J ^a   Latham, Hallie A ^a   Owen, David A ^a   Stein, Karin A ^a   Warnet, Ronald ^a,c  

^a CARLETON COLLEGE   (United States)

^b STATE UNIVERSITY OF NEW YORK   (United States)

^c SIMPSON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYRIC ACID DERIVATIVE; DEUTERIUM;

ARTICLE; IN VITRO STUDY; ISOTOPE LABELING; MOLECULAR DYNAMICS; PROTON TRANSPORT;

EID: 0031024779     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962631s     Document Type: Article

References (66)

1. Gerlt, J. A.; Gassman, P. G. Biochemistry 1993, 32, 11943-11952.
2. Mohrig, J. R.; Moerke, K. A.; Cloutier, D. M.; Lane, B. D.; Person, E. C.; Onasch, T. B. Science 1995, 269, 527-529.
3. Eliel, E. L.; Wilen, S. H. Stereochemistry of Carbon Compounds; Wiley-Interscience, 1994; Chapter 12.
4. (a) Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166.
5. (b) Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108-1117.
6. Bach, R. D.; Badger, R. C.; Lang, T. J. J. Am. Chem. Soc. 1979, 101, 2845-2848.
7. McGarvey, G. L.; Williams, J. M. J. Am. Chem. Soc. 1985, 107, 1435-1437.
8. Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 3353-3361.
9. Crump, R. A. N. C.; Fleming, I.; Hill, J. H. M.; Parker, D.; Reddy, N. L.; Waterson, D. J. Chem. Soc., Perkin Trans. 1 1992, 3277-3294.
10. (a) Zimmerman, H. E. Acc. Chem. Res. 1987, 20, 263-268.
11. (b) Zimmerman, H. E.; Chang, W.-H. J. Am. Chem. Soc. 1959, 81, 3634-3643.
12. Gerlach, U.; Haubenreich, T.; Hünig, S.; Keita, Y. Chem. Ber. 1993, 126, 1205-1215.
13. Mohrig, J. R.; Lee, P. K.; Stein, K. A.; Mitton, M. J.; Rosenberg, R. E. J. Org. Chem. 1995, 60, 3529-3532.
14. Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654.
15. (a) Collum, D. B. Acc. Chem. Res. 1992, 25, 448-454.
16. (b) Krom, J. A.; Streitwieser, A. J. Am.Chem. Soc. 1992, 114, 8747-8748.
17. (c) Abbotto, A.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 6358-6359.
18. (a) Mohrig, J. R.; Fu, S. S.; King, R. W.; Warnet, R.; Gustafson, G. J. Am. Chem. Soc. 1990, 112, 3665-3667.
19. (b) Mohrig, J. R.; Franklin, S. J.; King, R. W.; Larson, C. J.; Hirose, C. B.; Frisbie, C. D.; Warnet, R. Abstracts of the 199th National Meeting of the American Chemical Society, Boston, MA, April 1990; paper ORGN 404.
20. Rosenberg, R. E.; Mohrig, J. R. J. Am. Chem. Soc. 1997, 119, xxxx-xxxx.
21. We thank Prof. Ian Fleming for providing this compound.
22. Bordwell, F. G.; Van Der Puy, M.; Vanier, N. R. J. Org. Chem. 1976, 41, 1883-1885.
23. Fishbein, J. C.; Jencks, W. P. J. Am. Chem. Soc. 1988, 110, 5087-5095.
24. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277-297.
25. The dihedral angle at C-2 of the α-cyanocarbanion conjugate base of acetonitrile was calculated to be 130.3° (tetrahedral = 120°, trigonal = 180°) using ab initio MP2 (fc)/6-31G* calculations as described in ref 17.
26. Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K.; Inagaki, S. J. Org. Chem. 1991, 56, 6556-6564.
27. Powell, S. G.; Wasserman, W. J. J. Am. Chem. Soc. 1957, 79, 1934-1938.
28. (a) Mohrig, J. R.; Vreede, P. J.; Schultz, S. C.; Fierke, C. A. J. Org. Chem. 1981, 46, 4655-4658.
29. (b) Mohrig, J. R.; Dabora, S. L.; Foster, T. F.; Schultz, S. C. J. Org. Chem. 1984, 49, 5179-5182.
30. Weedon, A. C. Can. J. Chem. 1984, 62, 1933-1939.
31. Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457-4470.
32. (a) Poulter, C. D.; Satterwhite, D. M. Biochemistry 1977, 16, 5470-5478.
33. (b) Abele, H.; Haas, A.; Lieb, M. Chem. Ber. 1986, 119, 3502-3506.
34. (a) Chiang, Y.; Kresge, A. J. Science 1991, 253, 395-400.
35. (b) Keeffe, J. R.; Kresge, A. J.; Schepp, N. P. J. Am. Chem. Soc. 1990, 112, 4862-4868.
36. (a) Gerlach, U.; Haubenreich, T.; Hünig, S. Chem. Ber. 1994, 127, 1981-1988.
37. (b) Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, VCH: Weinheim, 1995; Vol. 7, pp 1-178.
38. (c) Nakamura, E.; Tanaka, K.; Fujimura, T.; Aoki, S.; Williard, P. G. J. Am. Chem. Soc. 1993, 115, 9015-9020.
39. Corey, E. J.; Sneen, R. A. J. Am. Chem. Soc. 1956, 78, 6269-6275.
40. Toullec, J. In Advances in Physical Organic Chemistry; Gold, V., Bethell, D., Eds.; Academic Press: London, 1982; Vol. 18, pp 1-77.
41. Fleming, I.; Lewis, J. J. J. Chem. Soc., Chem. Commun. 1985, 149-151.
42. (a) Kozikowski, A. P.; Ghosh, A. K. J. Am. Chem. Soc. 1982, 104, 5788-5789.
43. (b) Hori, K.; Higuchi, S.; Kamimura, A. J. Org. Chem. 1990, 55, 5900-5905.
44. (a) Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650-663.
45. (b) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 666-671.
46. Kawasaki, H.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1985, 26, 3031-3034.
47. Bott, G.; Field, L. D.; Sternhell, S. J. Am. Chem. Soc. 1980, 102, 5618-5626.
48. (a) Charton, M. J. Am. Chem. Soc. 1969, 91, 615-618.
49. (b) Della, E. W. J. Am. Chem. Soc. 1967, 89, 5221-5224.
50. Fleming, I.; Lewis, J. J. J. Chem. Soc., Perkin Trans. 1 1992, 3257-3266.
51. (a) Chiang, Y.; Hojatti, M.; Keeffe, J. R.; Kresge, A. J.; Schepp, N. P.; Wirz, J. J. Am. Chem. Soc. 1987, 109, 4000-4009.
52. (b) Chiang, Y.; Kresge, A. J.; Walsh, P. A. J. Am. Chem. Soc. 1986, 108, 6314-6320.
53. Apeloig, Y.; Karni, M.; Rappoport, Z. J. Am. Chem. Soc. 1983, 105, 2784-2793.
54. Michael, A. Ber. Dtsch. Chem. Ges. 1900, 33, 3748.
55. Elderfield, R. C.; Claflin, E. F.; Mertel, H. E.; McCurdy, O. L.; Mitch, R. T.; VerNooy, C. D.; Wark, B. H.; Wempen, I. M. J. Am. Chem. Soc. 1955, 77, 4819-4822.
56. Rupe, H.; van Walraven, F. Helv. Chim. Acta 1930, 13, 361-377.
57. Croxall, W. J.; Van Hook, J. O. J. Am. Chem. Soc. 1950, 72, 803-808.
58. Turner, E. E.; Turner, L. J. Chem. Soc. 1951, 2543-2545.
59. Chalchat, J.-C.; Theron, F.; Vessiere, R. Ann. Chim. 1971, 269-274.
60. Taschner, M. J.; Rosen, T.; Heathcock, C. H. In Organic Syntheses; Kende, A. S., Ed.; Wiley, 1986; Vol. 64, pp 108-113.
61. Truce, W. E.; Tichenor, G. J. J. Org. Chem. 1972, 37, 2391-2396.
62. Chalchat, J.-C.; Theron, F. Bull. Soc. Chim. France 1973, 3361-3366.
63. Weinges, K.; Kromm, E. Liebigs Ann. Chem. 1985, 90-102.
64. Levene, P. A.; Marker, R. E. J. Biol. Chem. 1935, 111, 299-312.
65. Boekelheide, V.; Fritz, H.; Ross, J. M.; Kaempfen, H. X. Tetrahedron 1964, 20, 33-41.
66. Bruylants, P. Bull. Soc. Chim. Belg. 1922, 31, 225-230.