Does activation of the anti proton, rather than concertedness, determine the stereochemistry of base-catalyzed 1,2-elimination reactions? Anti stereospecificity in E1cB eliminations of β-3-trifluoromethylphenoxy esters, thioesters, and ketones

Journal of Organic Chemistry

Volumn 77, Issue 6, 2012, Pages 2819-2828

  Mohrig, Jerry R ^a   Beyer, Brandon G ^a   Fleischhacker, Angela S ^a   Ruthenburg, Alex J ^a   John, Seth G ^a   Snyder, Daniel A ^a   Nyffeler, Paul T ^a   Noll, Robert J ^a   Penner, Nicholas D ^a   Phillips, Laura A ^a   Hurley, Heidi L S ^a   Jacobs, Jon S ^a   Treitel, Corinna ^a   James, Thomas L ^a   Montgomery, Martha P ^a  

^a CARLETON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-PROTONS; CARBONYL SUBSTRATES; DIASTEREOMERS; ELIMINATION REACTION; ENOLATE INTERMEDIATES; HEXANONE; HYPERCONJUGATION; LEAVING GROUPS; NMR DATA; STEREOSPECIFICITY; THIOESTERS;

CATALYSIS; KETONES; ORGANIC COMPOUNDS; PROTONS; STEREOCHEMISTRY; STEREOSELECTIVITY;

SUBSTRATES;

BETA 3 TRIFLUOROMETHYLPHENOXY ESTER; BUTYRIC ACID DERIVATIVE; CARBONYL DERIVATIVE; DEUTERIUM; ESTER; ISOTOPE; KETONE; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DEUTERON NUCLEAR MAGNETIC RESONANCE; DIASTEREOISOMER; ISOMER; KINETICS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; ESTERS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHENYL ETHERS; PROTONS; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; TOSYL COMPOUNDS;

EID: 84858648330     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300053w     Document Type: Article

References (53)

1. Saunders, W. H., Jr. Acc. Chem. Res. 1976, 9, 19-25
2. Mohrig, J. R.; Carlson, H. K.; Coughlin, J. M.; Hofmeister, G. E.; McMartin, L. A.; Rowley, E. G.; Trimmer, E. E.; Wild, A. J.; Schultz, S. C. J. Org. Chem. 2007, 72, 793-798
3. Mohrig, J. R.; Alberg, D. G.; Cartwright, C. H.; Pflum, M. K. H.; Aldrich, J. S.; Anderson, J. K.; Anderson, S. R.; Fimmen, R. L.; Snover, A. K. Org. Biomol. Chem. 2008, 6, 1641-1646
4. Kim, Y.; Mohrig, J. R.; Truhlar, D. G. J. Am. Chem. Soc. 2010, 132, 11071-11082
5. Gandler, J. R. Mechanisms of Base-Catalyzed Alkene-Forming 1,2-Eliminations. In The Chemistry of Doubly-Bonded Functional Groups; Patai, S., Ed.; Wiley & Sons: New York, 1989; pp 733-797.
6. Saunders, W. H., Jr.; Cockerill, A. F. Mechanisms of Elimination Reactions; Wiley & Sons: New York, 1973; Chapter 3, pp 105-163.
7. Gronert, S. J. Am. Chem. Soc. 1992, 114, 2349-2354
8. Saunders, W. H., Jr. J. Org. Chem. 2000, 65, 681-684
9. Dohner, B. R.; Saunders, W. H., Jr. J. Am. Chem. Soc. 1986, 108, 245-247
10. Cristol, S. J. J. Am. Chem. Soc. 1947, 69, 338-342
11. Cristol, S. J.; Hause, N. L.; Meek, J. S. J. Am. Chem. Soc. 1951, 73, 674-679
12. Hanhart, W.; Ingold, C. K. J. Chem. Soc. 1927, 997-1020
13. Hughes, E. D.; Ingold, C. K. Trans. Faraday Soc. 1941, 37, 657-685
14. Bartsch, R. A.; Závada, J. Chem. Rev. 1980, 80, 453-494
15. Mohrig, J. R.; Rosenberg, R. E.; Apostol, J. W.; Bastienaansen, M.; Evans, J. W.; Franklin, S. J.; Frisbie, C. D.; Fu, S. S.; Hamm, M. L.; Hirose, C. B.; Hunstad, D. A.; James, T. L.; King, R. W.; Larson, C. J.; Latham, H. A.; Owen, D. A.; Stein, K. A.; Warnet, R. J. Am. Chem. Soc. 1997, 119, 479-486
16. Poulter, C. D.; Satterwhite, D. M. Biochemistry 1977, 16, 5470-5478
17. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818
18. Taillier, C.; Bellosta, V.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2145-2147
19. nd ed.; Academic Press: New York, 1980; pp 149-163.
20. Altona, C.; Francke, R.; de Haan, R.; Ippel, J. H.; Daalmans, G. J.; Hoekzema, A. J. A. W.; van Wijk, J. Magn. Reson. Chem. 1994, 32, 670-678
21. Lin, S.; Saunders, W. H., Jr. J. Am. Chem. Soc. 1994, 116, 6107-6110
22. Gandler, J. R.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 1937-1951
23. Ryberg, P.; Matsson, O. J. Am. Chem. Soc. 2001, 123, 2712-2718
24. Lienhard, G. E.; Wang, F. C. J. Am. Chem. Soc. 1968, 90, 3781-3787
25. Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1996, 118, 3129-3141
26. Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1992, 114, 10297-10302
27. Chiang, Y.; Kresge, A. J.; Tang, Y. S.; Wirz, J. J. Am. Chem. Soc. 1984, 106, 460-462
28. Fukui, K.; Fujimoto, H. Tetrahedron Lett. 1965, 48, 4303-4307
29. McLennan, D. J. Quart. Rev. (London) 1967, 21, 490-506
30. th ed.; Wiley-Interscience: New York, 2007; pp 1489-1493.
31. Fishbein, J. C.; Jencks, W. P. J. Am. Chem. Soc. 1988, 110, 5075-5086
32. Fedor, L. R.; Glave, W. R. J. Am. Chem. Soc. 1971, 93, 985-989
33. Crosby, J.; Stirling, C. J. M. J. Chem. Soc. (B) 1970, 671-679
34. Crosby, J.; Stirling, C. J. M. J. Chem. Soc. (B) 1970, 679-686
35. Cavestri, R. C.; Fedor, L. R. J. Am. Chem. Soc. 1970, 92, 4610-4613
36. Stirling, C. J. M. Acc. Chem. Res. 1979, 12, 198-203
37. Boyd, D. B. J. Org. Chem. 1985, 50, 885-886
38. Martell, A. E.; Smith, R. M. Critical Stability Constants; Plenum Publishing: New York, 1977; Vol 3.
39. Liotta, C. L.; Smith, D. F., Jr.; Hopkins, H. P., Jr.; Rhodes, K. A. J. Phys. Chem. 1972, 76, 1909-1912
40. Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301-308
41. Amyes, T. L.; Richard, J. P. Proton Transfer to and from Carbon in Model Reactions. In Hydrogen Transfer Reactions; Hynes, J. T.; Klinman, J. P.; Limbach, H. H.; Schowen, R. L., Eds.; Wiley-VCH: Weinheim, 2007; Vol. 3, pp 949-973.
42. Hoffmann, R.; Radom, L.; Pople, J. A.; Schleyer, P. v. R.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221-6223
43. Apeloig, Y.; Rappoport, Z. J. Am. Chem. Soc. 1979, 101, 5095-5098
44. Karni, M.; Bernasconi, C. F.; Rappoport, Z. J. Org. Chem. 2008, 73, 2980-2994
45. King, J. F.; Rathore, R.; Guo, Z.; Li, M.; Payne, N. C. J. Am. Chem. Soc. 2000, 122, 10308-10324
46. King, J. F.; Li, M.; Cheung, A. Z.; Dave, V.; Payne, N. C. Can. J. Chem. 2003, 81, 638-646
47. Thibblin, A.; Ahlberg, P. J. Am. Chem. Soc. 1977, 99, 7926-7930
48. Meng, Q.; Thibblin, A. J. Chem. Soc., Perkin Trans. 2 1998, 583-589
49. Reference 5, pp 742-743.
50. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; p 591.
51. Apeloig, Y.; Karni, M.; Rappoport, Z. J. Am. Chem. Soc. 1983, 105, 2784-2793
52. Correlation Analysis in Chemistry-Recent Advances; Chapman, N. B.; Shorter, J., Eds.; Plenum Press: London, 1978.
53. Bienvenüe, A. J. Am. Chem. Soc. 1973, 95, 7345-7353