Steric course of the electrophilic substitution of a lithiocarbanion generated from (S,E)-1-phenylbut-2-en-1-yl diisopropylcarbamate and solvent effects

European Journal of Organic Chemistry

Volumn , Issue 32, 2011, Pages 6553-6557

  Ikemoto, Hidaka ^a   Sasaki, Michiko ^a   Kawahata, Masatoshi ^b   Yamaguchi, Kentaro ^b   Takeda, Kei ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Carbanions; Electrophilic substitution; Reaction mechanisms; Reactive intermediates; Solvent effects

Indexed keywords

EID: 80155193149     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100970     Document Type: Article

References (31)

1. D. Hoppe, The Chemistry of Organolithium Compounds, vol. 1 (Eds.:, Z. Rappoport, I. Marek), Wiley, Chichester, 2004, pp. 1055-1164.
2. D. Hoppe, F. Marr, M. Brüggemann, Organolithiums in Enantioselective Synthesis (Ed.:, D. M. Hodgson), Springer, New York, 2003, pp. 61-137.
3. D. M. Hodgson, K. Tomooka, E. Gras, Organolithiums in Enantioselective Synthesis (Ed.:, D. M. Hodgson), Springer, New York, 2003, pp. 217-250.
4. J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Oxford, 2002, pp. 169-240.
5. A. Basu, S. Thayumanavan, Angew. Chem. 2002, 114. 740-763
6. Angew. Chem. Int. Ed. 2002, 41, 716-738.
7. V. K. Aggarwal, Angew. Chem. 1994, 106, 185;
8. Angew. Chem. Int. Ed. Engl. 1994, 33, 175-177.
9. E. Buncel, J. M. Dust, Carbanion Chemistry: Structures and Mechanisms, American Chemical Society, Washington DC, 2003, pp. 119-162.
10. R. E. Gawley, Stereochemical Aspects of Organolithium Compounds, Topics in Stereochemistry (Eds.:, R. E. Gawley, J. Siegel), Wiley, New York, 2010;, Vol. 26, Chapter 3.
11. R. W. Hoffmann, Stereochemical Aspects of Organolithium Compounds, Topics in Stereochemistry (Eds.: R. E. Gawley, J. Siegel), Wiley, New York, 2010, vol. 26, chapter 5.
12. H. Ikemoto, M. Sasaki, K. Takeda, Eur. J. Org. Chem. 2010, 6643-6650.
13. A. Carstens, D. Hoppe, Tetrahedron 1994, 50, 6097-6108.
14. D. Hoppe, A. Carstens, T. Kramer, Angew. Chem. 1990, 102, 1455-1456;
15. Angew. Chem. Int. Ed. Engl. 1990, 29, 1422-1424.
16. C. Derwing, H. Frank, D. Hoppe, Eur. J. Org. Chem. 1999, 3519-3524.
17. D. Hoppe, B. Kaiser, O. Stratmann, R. Fröhlich, Angew. Chem. 1997, 109, 2872-2874; . Also see
18. Angew. Chem. Int. Ed. Engl. 1997, 36, 2784-2786
19. R. E. Gawley, Q. J. Zhang, J. Org. Chem. 1995, 60, 5763-5769.
20. N. C. Faibish, Y. S. Peak, S. Lee, P. Beak, J. Am. Chem. Soc. 1997, 119, 11561-11570.
21. S. Thayumanavan, S. Lee, C. Liu, P. Beak, J. Am. Chem. Soc. 1994, 116, 9755-9756.
22. C. Strohmann, B. C. Abele, K. Lehmen, Angew. Chem. 2005, 117, 3196-3199;
23. Angew. Chem. Int. Ed. 2005, 44, 3136-3139.
24. H. Ott, C. Däschlein, D. Leusser, D. Schildbach, T. Seibel, D. Stalke, C. Strohmann, J. Am. Chem. Soc. 2008, 130, 11901-11911.
25. M. Binanzer, G. Fang, V. Aggarwal, Angew. Chem. 2010, 122, 5268-5271;
26. Angew. Chem. Int. Ed. 2010, 49, 4264-4268.
27. M. Sasaki, M. Higashi, H. Masu, K. Yamaguchi, K. Takeda, Org. Lett. 2005, 7, 5913-5915.
28. M. Sasaki, H. Ikemoto, M. Kawahata, K. Yamaguchi, K. Takeda, Chem. Eur. J. 2009, 15, 4663-4666.
29. M. Seppi, R. Kalkofen, J. Reupohl, R. Fröhlich, D. Hoppe, Angew. Chem. 2004, 116, 1447-1451
30. Angew. Chem. Int. Ed. 2004, 43, 1423-1424.
31. R. Hof, R. M. Kellogg, J. Chem. Soc. Perkin Trans. 1 1996, 2051-2060.