A catalytic enantioselective electron transfer reaction: Titanocene- catalyzed enantioselective formation of radicals from meso-Epoxides

Angewandte Chemie - International Edition

Volumn 38, Issue 19, 1999, Pages 2909-2910

  Gansäuer, Andreas ^a   Lauterbach, Thorsten ^a   Bluhm, Harald ^a   Noltemeyer, Mathias ^b  

^a UNIVERSITY OF FREIBURG   (Germany)

^b NONE

Author keywords

Enantioselectivity; Epoxides homogeneous catalysis; Radical reactions; Titanium

Indexed keywords

TITANOCENE;

ARTICLE; CATALYSIS; CHIRALITY; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; ENANTIOMER; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0038212942     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991004)38:19<2909::AID-ANIE2909>3.0.CO;2-Y     Document Type: Article

References (23)

1. a) A. Gansäuer, M. Pierobon, H. Bluhm, Angew. Chem. 1998, 110, 107; Angew. Chem. Int. Ed. 1998, 35, 101;
2. a) A. Gansäuer, M. Pierobon, H. Bluhm, Angew. Chem. 1998, 110, 107; Angew. Chem. Int. Ed. 1998, 35, 101;
3. b) A. Gansäuer, H. Bluhm, Chem. Commun. 1998, 2143;
4. c) A. Gansäuer, H. Bluhm, M. Pierobon, J. Am. Chem. Soc. 1998, 120, 12849.
5. a) A. Gansäuer, D. Bauer, J. Org. Chem. 1998, 63, 2070;
6. b) A. Gansäuer, D. Bauer, Eur. J. Org. Chem. 1998, 2673.
7. Review: A. Gansäuer, Synlett 1998, 801.
8. For some enantioselective radical reactions based on different concepts, see a) J. H. Wu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029;
9. b) M. P. Sibi, J. Ji, J. H. Wu, S. Gürtler, N. A. Porter, J. Am. Chem. Soc. 1996, 118, 9200;
10. c) M. Blumenstein, K. Schwartzkopf, J. O. Metzger, Angew. Chem. 1997, 109, 245; Angew. Chem. Int. Ed. Engl. 1997, 36, 225; K. Mikami, M. Yamaoka, Tetrahedron Lett. 1998, 39, 4501.
11. c) M. Blumenstein, K. Schwartzkopf, J. O. Metzger, Angew. Chem. 1997, 109, 245; Angew. Chem. Int. Ed. Engl. 1997, 36, 225; K. Mikami, M. Yamaoka, Tetrahedron Lett. 1998, 39, 4501.
12. c) M. Blumenstein, K. Schwartzkopf, J. O. Metzger, Angew. Chem. 1997, 109, 245; Angew. Chem. Int. Ed. Engl. 1997, 36, 225; K. Mikami, M. Yamaoka, Tetrahedron Lett. 1998, 39, 4501.
13. R. L. Halterman in Metallocenes, Vol. 1 (Eds.: A. Togni, R. L. Halterman), WILEY-VCH, Weinheim, 1998, p. 455.
14. R. L. Halterman, K. P. C. Vollhardt, Organometallics 1988, 7, 883.
15. -3, 3454 independent reflections, R1 = 0.0473 for I > 2σ(I), wR2 = 0.1101 for all data. The structure was solved by direct methods and refined with anisotropic temperature factors for all non-hydrogen atoms; hydrogen atoms were added in idealized positions and included in the refinement. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-118965. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
16. a) M. Bochman in Comprehensive Organometallic Chemistry II, Vol. 4 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 221, 273;
17. b) T. C McKenzie, R. D. Scanner, J. E. Bercaw, J. Organomet. Chem. 1975, 102, 457;
18. c) J. W. Pattiasina, H. J. Heeres, F. van Bolhuis, A. Meetsma, J. H. Teuben, A. L. Speek, Organometallics 1987, 6, 1004.
19. a) B. Giese, Angew. Chem. 1989, 101, 993; Angew. Chem. Int. Ed. Engl. 1989, 28, 969;
20. a) B. Giese, Angew. Chem. 1989, 101, 993; Angew. Chem. Int. Ed. Engl. 1989, 28, 969;
21. b) B. Giese, K. Heuck, H. Lenhardt, Chem. Ber. 1984, 117, 2132.
22. a) W. A. Nugent, T. V. RajanBabu, J. Am. Chem. Soc. 1988, 110, 8561;
23. b) T. V. RajanBabu, W. A. Nugent, J. Am. Chem. Soc. 1994, 116, 986.