Enantiomerically enriched 'carbanions': Studies on the stereochemical course of selective transformations of metal alkyls

Journal of Organometallic Chemistry

Volumn 661, Issue 1-2, 2002, Pages 149-158

  Strohmann, Carsten ^a   Abele, Bors C ^a   Lehmen, Klaus ^a   Villafañe, Fernando ^b   Sierra, Luisa ^b   Martín Barrios, Susana ^b   Schildbach, Daniel ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Carbanion; Diastereomerically enriched; Organolithium; Organometallic chemistry; Solid state structures

Indexed keywords

ALKYL GROUP; AMINE; CADMIUM; GALLIUM; HALIDE; ION; LITHIUM DERIVATIVE; MAGNESIUM; MERCURY; ORGANOMETALLIC COMPOUND; PALLADIUM; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; DIASTEREOISOMER; ENANTIOMER; ION TRANSPORT; SOLID STATE; STEREOCHEMISTRY;

EID: 0036828509     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(02)01825-9     Document Type: Article

References (37)

1. A. Basu, S. Thayumanavan, Angew. Chem. Int. Ed. Engl. 41 (2002) 716 (and cited literature therein);
2. D. Hoppe, T. Hense, Angew. Chem. Int. Ed. Engl. 36 (1997) 2282 (and cited literature therein).
3. O. Stratmann, B. Kaiser, R. Fröhlich, O. Meyer, D. Hoppe, Chem. Eur. J. 7 (2001) 423;
4. T. Heinl, S. Retzow, D. Hoppe, G. Fraenkel, A. Chow, Chem. Eur. J. 5 (1999) 3464;
5. C. Derwing, H. Frank, D. Hoppe, Eur. J. Org. Chem. (1999) 3519;
6. J. Schwerdtfeger, S. Kolczewski, B. Weber, R. Fröhlich, D. Hoppe, Synthesis 9 (1999) 573;
7. E. Würthwein, K. Behrens, D. Hoppe, Chem. Eur. J. 5 (1999) 3459.
8. T.A. Johnson, M.D. Curtis, P. Beak, J. Am. Chem. Soc. 123 (2001) 1004;
9. P. Beak, D.R. Anderson, M.D. Curtis, J.M. Laumer, D.J. Pippel, G.A. Weisenburger, Acc. Chem. Res. 33 (2000) 715;
10. G.A. Weisenburger, N.C. Faibish, D.J. Pippel, P. Beak, J. Am. Chem. Soc. 121 (1999) 9522;
11. D.J. Pippel, G.A. Weisenburger, S.R. Wilson, P. Beak, Angew. Chem. Int. Ed. Engl. 37 (1998) 2522.
12. H.J. Reich, K.J. Kulicke, J. Am. Chem. Soc. 118 (1996) 273.
13. G. Fraenkel, J.H. Duncan, K. Martin, J. Wang, J. Am. Chem. Soc. 121 (1999) 10538;
14. G. Fraenkel, K. Martin, J. Am. Chem. Soc. 117 (1995) 10336.
15. C. Lambert, P.v.R. Schleyer, L. Brandsma, in: M. Hanack (Ed.), Methoden Org. Chem., 4th ed., Houben-Weyl: 1952-1993, vol. E19d, Thieme Verlag, Stuttgart, 1993, pp. 1-113.
16. See also: C. Strohmann, B.C. Abele, in: N. Auner, J. Weis (Eds.), Organosilicon Chemistry III, Wiley-VCH, Weinheim (Germany), 1998, pp. 206-210.
17. E. Keller, SCHAKAL-99, University of Freiburg, Freiburg, Germany, 1999.
18. C. Strohmann, D. Schildbach, Acta Crystallogr. C58 (2002), m447.
19. See also: G.-J.M. Gruter, G.P.M. van Klink, O.S. Akkerman, F. Bickelhaupt, Chem. Rev. 95 (1995) 2405;
20. H. Schumann, S. Freitag, F. Girgsdies, H. Hemling, G. Kociok-Köhn, Eur. J. Inorg. Chem. (1998) 245;
21. M.J. Henderson, R.I. Papasergio, C.L. Raston, A.H. White, M.F. Lappert, J. Chem. Soc. Chem. Commun. (1986) 672;
22. S.S. Al-Juaid, C. Eaborn, P.B. Hitchcock, C.A. McGeary, J.D. Smith, J. Chem. Soc. Chem. Commun. (1989) 273;
23. S.S. Al-Juaid, C. Eaborn, P.B. Hitchcock, K. Kundu, C.A. McGeary, J.D. Smith, J. Organomet. Chem. 480 (1994) 199;
24. C. Eaborn, K. Izod, D.J. Smith, J. Organomet. Chem. 500 (1995) 89.
25. W. Uhl, L. Cuypers, K. Schüler, T. Spies, C. Strohmann, K. Lehmen, Z. Anorg. Allg. Chem. 626 (2000) 1526.
26. D. Schildbach, L. Sierra, S. Martín-Barrios, K. Lehmen, F. Villafañe, C. Strohmann, Organometallics, in press.
27. P.M. Maitlis, P. Espinet, M.J.H. Rusell, in: G. Wilkinson, F.G.A. Stone, E.W. Abel (Eds.), Comprehensive Organometallic Chemistry, vol. 6, Pergamon, Oxford (UK), 1982, pp. 333-334.
28. T.H. Chan, P. Pellon, J. Am. Chem. Soc. 111 (1989) 8737;
29. T.H. Chan, S. Lamothe, Tetrahedron Lett. 32 (1991) 1847;
30. T.H. Chan, K.T. Nwe, J. Org. Chem. 57 (1992) 6107.
31. C. Strohmann, K. Lehmen, K. Wild, D. Schildbach, Organometallics 21 (2002) 3079.
32. For examples see: F. Marr, R. Fröhlich, D. Hoppe, Org. Lett. 1 (1999) 2081;
33. D. Hoppe, B. Kaiser, O. Stratmann, R. Froehlich, Angew. Chem. Int. Ed. Engl. 36 (1997) 2784;
34. N.C. Faibish, Y.S. Park, S. Lee, P. Beak, J. Am. Chem. Soc. 119 (1997) 11561;
35. M.D. Curtis, P. Beak, J. Org. Chem. 64 (1999) 2996;
36. F. Hammerschmidt, A. Hanninger, B.C. Simov, H. Völlenkle, A. Werner, Eur. J. Org. Chem. (1999) 3511.
37. S. Portmann, MOLEKEL, Version 4.1. win-32, ETH Zuerich, Zuerich, Switzerland, 2001.