On the reason for opposite diastereoselectivities of benzyllithium compounds containing lithium amide and lithium alkoxide functionalities

Tetrahedron

Volumn 52, Issue 30, 1996, Pages 10025-10042

  Mück Lichtenfeld, Christian ^a   Ahlbrecht, Hubertus ^a  

^a Inst fur Org Chem der J   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOLITHIUM COMPOUND;

ARTICLE; CALCULATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030598055     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00535-2     Document Type: Article

References (33)

1. 1. Diplomarbeit, Gießen 1994.
2. 3. P.R. Peoples, J.B. Grutzner, J. Am. Chem. Soc. 1980, 102, 4709.
3. 4. R.W. Hoffmann, T. Rühl, F. Chemla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719.
4. 5. T. Kato, S. Marumoto, T. Sato, I. Kuwajima, Synlett 1990, 671.
5. 6. D. Hoppe, A. Carstens, T. Krämer, Angew. Chem. 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424.
6. 6. D. Hoppe, A. Carstens, T. Krämer, Angew. Chem. 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424.
7. 7. E.D. Jemmis, J. Chandrasekhar, P.v.R. Schleyer, J. Am. Chem. Soc. 1979, 101, 527.
8. 8. S. Klein, I. Marek, J.-F. Normant, J. Org. Chem. 1994, 59, 2925.
9. 9. C. Mück-Lichtenfeld, H. Ahlbrecht, Manuscript in preparation.
10. 10. S. Klein, I. Marek, J.-F. Poisson, J.-F. Normant, J. Am. Chem. Soc. 1995, 117, 8853.
11. 11. J. Barluenga, F.J. Fañanás, F. Foubelo, M. Yus, J. Chem. Soc., Chem. Commun. 1988, 1135.
12. 12. J. Almena, F. Foubelo, M. Yus, Tetrahedron 1994, 50, 5775.
13. 13. a) W. Bauer, D. Seebach, Helv. Chim. Acta 1984, 67, 1972.
14. b) H. Sommer, Dissertation, Gießen 1990.
15. 14. E.M. Arnett, K.D. Moe, J. Am. Chem. Soc. 1991, 113, 7288.
16. 15. D.B. Collum, Acc. Chem. Res. 1993, 26, 227 (and references cited therein).
17. 16. J.J.P. Stewart, J. Comp. Chem. 1989, 10, 209, 221.
18. 17. M.J.S. Dewar, W. Thiel, J. Am. Chem. Soc. 1977, 99, 4899.
19. 18. E. Anders, R. Koch, P. Freunscht, J. Comp. Chem. 1993, 14, 1301.
20. 19. R. Koch, E. Anders, J. Org. Chem. 1994, 59, 4529.
21. 20. H. Ahlbrecht, unpublished results.
22. 21. P.v.R. Schleyer, A.J. Kos, E. Kaufmann, J. Am. Chem. Soc. 1983, 105, 7617.
23. 22. A. Streitwieser, Jr., Acc. Chem. Res. 1984, 17, 353.
24. 23. S.P. Patterman, I.L. Karle, G.D. Stucky, J. Am. Chem. Soc. 1970, 92, 1150.
25. 24. H. Ahlbrecht, J. Harbach, T. Hauck, H.-O. Kalinowski, Chem. Ber. 1992, 125, 1753.
26. 25. A. Sygula, P.W. Rabideau, J. Am. Chem. Soc. 1992, 114, 821.
27. 26. H. Günther, NMR-Spektroskopie, Stuttgart, New York 1992, p. 108.
28. 27. We used the program CLATUX: G. Binsch, Topics in Stereochemistry 1968, 3, 97. Half-height linewidths were chosen to be 2.2 Hz (left signal) and 2.8 Hz (right signal).
29. 28. N. De Kimpe, E. Stanoeva, R. Verhé, N. Schamp, Synthesis 1988, 587.
30. 29. W.G. Kofron, L.M. Baczlawksi, J. Org. Chem. 1976, 41, 1879.
31. 30. Mopac 93: QPCE 455 / IBMW, QPCE, Creative Arts Building 181, Indiana Univ. Bloomington IN, 47405, USA.
32. 31. VAMP: G. Rauhut, J. Chandrasekhar, T. Clark, Erlangen 1991.
33. 32. Gaussian 94, Revision B.1, M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, Gaussian, Inc., Pittsburgh PA, 1995.