"stereoelectronic umpolung": Converting a p-donor into a σ-acceptor via electron injection and a conformational change

Organic Letters

Volumn 15, Issue 9, 2013, Pages 2238-2241

  Peterson, Paul W ^a   Shevchenko, Nikolay ^a   Alabugin, Igor V ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84877119620     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400813d     Document Type: Article

References (38)

1. Mohamed, R. K.; Peterson, P. W.; Alabugin, I. V. Chem. Rev. 2013, DOI: 10.1021/cr4000682.
2. Bergman, R. G. Acc. Chem. Res. 1973, 6, 25
3. Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881
4. Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995
5. Myers, A. G.; Dragovich, P. S.; Kuo, E. Y. J. Am. Chem. Soc. 1992, 114, 9369
6. Sullivan, R. W.; Coghlan, V. M.; Munk, S. A.; Reed, M. W.; Moore, H. W. J. Org. Chem. 1994, 59, 2276
7. Engels, B.; Lennartz, C.; Hanrath, M.; Schmittel, M.; Strittmatter, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2067
8. Schmittel, M.; Rodriguez, D.; Steffen, J. P. Angew Chem., Int. Ed. 2000, 39, 2067
9. Peterson, P. W.; Mohamed, R. K.; Alabugin, I. V. Eur. J. Org. Chem. 2013, DOI: 10.1002/ejoc.201201656
10. Bowles, D. M.; Palmer, G. J.; Landis, C. A.; Scott, J. L.; Anthony, J. E. Tetrahedron 2001, 57, 3753
11. John, J. A.; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 5011
12. Chen, X.; Tolbert, L. M.; Hess, D. W.; Henderson, C. Macromolecules 2001, 34, 4104
13. Choy, N.; Kim, C. S.; Ballestero, C.; Argitas, L.; Diez, C.; Lichtenberg, F.; Shapiro, L.; Russell, K. C. Tetrahedron Lett. 2000, 41, 6995
14. Alabugin, I. V.; Manoharan, M.; Kovalenko, S. V. Org. Lett. 2002, 4, 1119
15. Zeidan, T.; Kovalenko, S. V.; Manoharan, M.; Alabugin, I. V. J. Org. Chem. 2006, 71, 962
16. Baroudi, A.; Mauldin, J.; Alabugin, I. V. J. Am. Chem. Soc. 2010, 133, 967
17. Alabugin, I. V.; Manoharan, M. J. Am. Chem. Soc. 2003, 125, 4495
18. Prall, M.; Wittkopp, A.; Schreiner, P. R. J. Phys. Chem. A 2001, 105, 9265
19. Vavilala, C.; Byrne, N.; Kraml, C. M.; Ho, D. M.; Pascal, R. A. J. Am. Chem. Soc. 2008, 130, 13549
20. Whitlock, H. W., Jr.; Sandvick, P. E.; Overman, L. E.; Reichardt, P. B. J. Org. Chem. 1969, 34, 879
21. Alabugin, I. V.; Kovalenko, S. V. J. Am. Chem. Soc. 2002, 124, 9052
22. Breiner, B.; Schlatterer, J. C.; Kovalenko, S. V.; Greenbaum, N. L.; Alabugin, I. V. Angew. Chem., Int. Ed. 2006, 45, 3666
23. Kovalenko, S. V.; Alabugin, I. V. Chem. Commun. 2005, 1444
24. Breiner, B.; Schlatterer, J. C.; Alabugin, I. V.; Kovalenko, S. V.; Greenbaum, N. L. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 13016
25. Yang, W.-Y.; Breiner, B.; Kovalenko, S. V.; Ben, C.; Singh, M.; LeGrand, S. N.; Sang, A. Q.-X.; Strouse, G. F.; Copland, J. A.; Alabugin, I. V. J. Am. Chem. Soc. 2009, 131, 11458
26. Yang, W.-Y.; Roy, S.; A., R.; Phrathep, B.; Rengert, Z.; Alabugin, I. V. J. Med. Chem. 2011, 54, 8501
27. Review: Breiner, B.; Kaya, K.; Roy, S.; Yang, W.-Y.; Alabugin, I. V. Org. Biomol. Chem. 2012, 10, 3974
28. 3SnH-mediated 5-exo-dig cyclizations of enediynes as described earlier: Kovalenko, S. V.; Peabody, S.; Manoharan, M.; Clark, R. J.; Alabugin, I. V. Org. Lett. 2004, 6, 2457
29. Peabody, S.; Breiner, B.; Kovalenko, S. V.; Patil, S.; Alabugin, I. V. Org. Biomol. Chem. 2005, 3, 218
30. Alabugin, I. V.; Gilmore, K.; Patil, S.; Manoharan, M.; Kovalenko, S. V.; Clark, R. J.; Ghiviriga, I. J. Am. Chem. Soc. 2008, 130, 11535
31. Byers, P.; Alabugin, I. V. J. Am. Chem. Soc. 2012, 134, 9609
32. Zeidan, T.; Manoharan, M.; Alabugin, I. V. J. Org. Chem. 2006, 71, 954
33. Alabugin, I. V.; Zeidan, T. A. J. Am. Chem. Soc. 2002, 124, 3175
34. Alabugin, I. V.; Gilmore, K. M; Peterson, P. W. WIREs Comput. Mol. Sci. 2011, 1, 109
35. Gold, B.; Dudley, G. B.; Alabugin, I. V. J. Am. Chem. Soc. 2013, 135, 1558
36. Gold, B.; Shevchenko, N.; Bonus, N.; Dudley, G. B.; Alabugin, I. V. J. Org. Chem. 2012, 77, 75
37. An interesting analogy is provided by the "law of increasing electron demand" in cationic processes: Brown, H. C. The Nonclassical Ion Problem; Plenum Press: New York, NY, 1977.
38. Alabugin, I. V. J. Org. Chem. 2000, 65, 3910