Discrimination of enantiotopic iodine atoms by an iodine/magnesium exchange reaction

Chemistry - A European Journal

Volumn 5, Issue 1, 1999, Pages 337-344

  Schulze, Volker ^a   Hoffmann, Reinhard W ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Carbenoids; Grignard reagents

Indexed keywords

ALKANE; ALKYLMAGNESIUM IODIDE DERIVATIVE; ALUMINUM DERIVATIVE; BENZALDEHYDE; DIIODOALKANE; DIMETHYLALUMINIUM CHLORIDE; EPOXIDE; GRIGNARD REAGENT; IODINE; IODINE DERIVATIVE; IODOHYDRIN DERIVATIVE; MAGNESIUM; MAGNESIUM DERIVATIVE; REAGENT; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; ATOM; ENANTIOMER; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0032926215     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990104)5:1<337::AID-CHEM337>3.0.CO;2-P     Document Type: Article

References (32)

1. For Part XXI see: H. C. Stiasny, V. P. W. Böhm, R. W. Hoffmann, Chem. Ber. 1997, 130, 341-346.
2. Houben-Weyl, Methods of Organic Chemistry, 4th ed; Stereoselective Synthesis (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, E21, 1995.
3. D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-3410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316.
4. D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-3410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316.
5. J. Villiéras, Organomet. Chem. Rev. A. 1971, 7, 81-94.
6. a) R. W. Hoffmann, M. Julius, F. Chemla, T. Ruhland, G. Frenzen, Tetrahedron 1994, 50, 6049-6060;
7. b) W. Klute, M. Krüger, R. W. Hoffmann, Chem. Ber. 1996, 129, 633-638.
8. a) J. Villiéras, Bull. Soc. Chim. Fr. 1967, 1520-1532;
9. b) D. Seyferth, R. L. Lambert Jr., E. M. Hanson, J. Organomet. Chem. 1970, 24, 647-661;
10. c) R. C. Hahn, J. Tompkins, Tetrahedron Lett. 1990, 31, 937-940;
11. d) C. DeLima, M. Julia, J.-N. Verpeaux, Synlett. 1992, 133-134;
12. e) R. W. Hoffmann, A. Kusche, Chem. Ber. 1994, 127, 1311-1316.
13. We thank Dr. R. Löwe for carrying out this experiment: R. Löwe, Dissertation, Universität Marburg, 1997.
14. a) D. J. Procter, M. Thornton-Pett, C. M. Rayner, Tetrahedron 1996, 52, 1841-1854;
15. b) M. Tanaka, I. Ogata, Bull. Chem. Soc. Jpn. 1975, 48, 1094.
16. W. F. Bailey, J. J. Patricia, J. Organomet. Chem. 1988, 352, 1-46.
17. G. Wittig, U. Schöllkopf, Tetrahedron 1958, 3, 91-93.
18. V. Schulze, M. Brönstrup, V. P. W. Böhm, P. Schwerdtfeger, M. Schimeczek, R. W. Hoffmann, Angew. Chem. 1998, 110, 869-871; Angew. Chem. Int. Ed. Engl. 1998, 37, 824-826.
19. V. Schulze, M. Brönstrup, V. P. W. Böhm, P. Schwerdtfeger, M. Schimeczek, R. W. Hoffmann, Angew. Chem. 1998, 110, 869-871; Angew. Chem. Int. Ed. Engl. 1998, 37, 824-826.
20. a) R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6008;
21. b) D. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232-240.
22. V. Schulze, R. Löwe, S. Fau, R. W. Hoffmann, J. Chem. Soc. Perkin Trans. 2 1998, 463-465.
23. V. Schulze, Dissertation, Universität Marburg, 1997.
24. J. L. von dem Bussche-Hünnefeld, D. Seebach, Tetrahedron 1992, 48, 5719-5730.
25. a) R. Hirsch, R. W. Hoffmann, Chem. Ber. 1992, 125, 975-982;
26. b) R. W. Hoffmann in Organic Synthesis via Organometallics (OSM4) (Eds.: D. Enders, H.-J. Gais, W. Keim), Vieweg, Braunschweig, 1993, pp. 79-91.
27. a) G. Wittig, G. Fuhrmann, Ber. Dtsch. Chem. Ges. 1940, 73, 1197-1218;
28. b) H. C. Stiasny, R. W. Hoffmann, Chem. Eur. J. 1995, 619-624.
29. H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249-330.
30. P. Charreau, M. Julia, J.-N. Verpeaux, Bull. Soc. Chim. Fr. 1990, 127, 275-282.
31. Y. Tamura, S. M. Bayomi, K. Sumoto, M. Ikeda, Synthesis 1977, 693-695.
32. P. Varelis, B. L. Johnson, Austr. J. Chem. 1995, 48, 1775-1779.