Lithiation/electrophilic quench of [η5-cyclohexadienylMn(CO) 3]: Versatile functionalization and resolution of planar chirality in the organomanganese series

Angewandte Chemie - International Edition

Volumn 45, Issue 21, 2006, Pages 3481-3484

  Jacques, Béatrice ^a   Chavarot, Murielle ^a   Rose Munch, Françoise ^a   Rose, Eric ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Arene ligands; Electrophilic addition; Enantiopure complexes; Lithiation; Manganese

Indexed keywords

COMPLEXATION; DERIVATIVES; MANGANESE; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

ARENE LIGANDS; ELECTROPHILIC ADDITION; ENANTIOPURE COMPLEXES; LITHIATION;

QUENCHING;

EID: 33746238111     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600689     Document Type: Article

References (29)

1. A. N. Nesmeyanov, N. E. Kolobova, K. N. Anisimov, Y. V. Markarov, Izv. Akad. Nauk. SSSR Ser. Khim. 1968, 2665-2665.
2. For recent reviews, see: a) M. F. Semmelhack in Comprehensive Organometallic Chemistry 11, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1017-1038;
3. b) F. Rose-Munch, E. Rose, Curr. Org. Chem. 1999, 3, 445-467;
4. c) A. Berger, J.-P. Djukic, C. Michon, Coord. Chem. Rev. 2002, 225, 215-238;
5. d) M. F. Semmelhack, A. Chlenov, Top. Organomet. Chem. 2004, 7, 21-42.
6. For recent reviews, see: a) K. F. McDaniel in Comprehensive Organometallic Chemistry II, Vol. 6 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, UK, 1995, pp. 93-107;
7. b) R. D. Pike, D. A. Sweigart, Coord. Chem. Rev. 1999, 187, 183-222;
8. c) A. R. Pape, K. P. Kaliappan, E. P. Kündig, Chem. Rev. 2000, 100, 2917-2940;
9. d) F. Rose-Munch, E. Rose, Eur. J. Inorg. Chem. 2002, 1269-1283.
10. T. Y. Lee, Y. K. Kang, Y. K. Chung, R. D. Pike, D. A. Sweigart, Inorg. Chim. Acta 1993, 214, 125-134.
11. F. Baissa, V. Gagliardini, F. Rose-Munch, E. Rose, Organometallics 1996, 15, 4373-4382.
12. A. Auffrant, D. Prim, F. Rose-Munch, E. Rose, S. Schouteeten, J. Vaissermann, Organometallics 2003, 22, 1898-1913.
13. a) J. F. Carpentier, F. Petit, A. Mortreux, V. Dufaud, J. M. Basset, J. Thivolle-Cazat, J. Mol. Catal. 1993, 81, 1-15;
14. b) D. Prim, B. Andrioletti, F. Rose-Munch, E. Rose, F. Couty, Tetrahedron 2004, 60, 3325-3347.
15. Y. K. Chung, P. G. Williard, D. A. Sweigart, Organometallics 1982, 1, 1053-1056.
16. The directed ortho metalation is a well-known methodology in organic synthesis; see for example; a) V. Snieckus, Chem. Rev. 1990, 90, 879-933;
17. b) M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256-2276;
18. Angew. Chem. Int. Ed. 2004, 43, 2206-2225.
19. R. Hoffmann, P. Hofmann, J. Am. Chem. Soc. 1976, 98, 598-604.
20. P. L. Pauson, J. A. Segal, J. Chem. Soc. Dalton Trans. 1975, 1677-1682.
21. -1, 4767 independent reflections, R = 0.0209, wR = 0.0241. The structure was solved by direct methods using SHELXS86 and refined with full-matrix least-squares technique on F using the CRYSTALS programs. CCDC-298751 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif.
22. W. H. Miles, P. M. Smiley, H. R. Brinkman, J. Chem. Soc. Chem. Commun. 1989, 1897-1899.
23. a) A. J. Pearson, P. Y. Zhu, W. J. Youngs, J. D. Bradshaw, D. B. McConville, J. Am. Chem. Soc. 1993, 115, 10376-10377;
24. b) A. J. Pearson, A. V. Gontcharov, P. Y. Zhu, Tetrahedron 1997, 53, 3849-3862.
25. S. U. Son, K. H. Park, S. J. Lee, H. Seo, Y. K. Chung, Chem. Commun. 2002, 1230-1231.
26. A. Alexakis, P. Mangeney, I. Marek, F. Rose-Munch, E. Rose, A. Semra, F. Robert, J. Am. Chem. Soc. 1992, 114, 8288-8290.
27. 3).
28. The planar chirality was assigned according to the extended Cahn-Ingold-Prelog (CIP) rules.
29. -1, 6866 independent reflections, R = 0.0303, wR = 0.0321. The structure was solved by direct methods using SHELXS86 and refined with full-matrix least-squares technique on F using the CRYSTALS programs. CCDC-298752 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data_request/cif.