Synthesis of planar chiral cobalt metallocenes by microwave-assisted diastereoselective complexation

Organometallics

Volumn 25, Issue 11, 2006, Pages 2899-2902

  Taylor, Caroline J ^a   Motevalli, Majid ^a   Richards, Christopher J ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; COBALT; COMPLEXATION; ESTERS; ETHERS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

CHIRAL METALLOCENES; DIASTEREOMERIC RATIOS; DIYNES; PROPARGYLIC ALCOHOLS;

ORGANOMETALLICS;

EID: 33745746379     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060015r     Document Type: Article

References (23)

1. (a) Colacot, T. J. Chem. Rev. 2003, 103, 3101.
2. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377.
3. See for example: (a) Bunz, U. H. F. J. Organomet. Chem. 2003, 683, 269.
4. (b) Chuard, T.; Deschenaux, R. Chimia 2003, 57, 597.
5. See for example: (a) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835.
6. (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568.
7. Schumann, H.; Stenzel, O.; Dechert, S.; Halterman, R. L. Organometallics 2001, 20, 1983.
8. Gleiter, R.; Kratz, D.; Ziegler, M. L.; Nuber, B. Tetrahedron Lett. 1990, 31, 6175.
9. (a) Bradley, A.; Motherwell, W. B.; Ujjainwalla, F. Chem. Commun. 1999, 917.
10. (b) Phannarath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561.
11. (c) Eckenberg, P.; Groth, U. Synlett 2003, 2188.
12. int = 0.0826, T = 120(2) K, final R indices for I > 2σ(I) R1 = 0.0630, wR2 = 0.1483 and for all data R1 = 0.1380, wR2 = 0.1829.
13. The reaction between cyclopentadienylcobalt dicarbonyl and diphenylacetylene under thermal conditions results in the formation of both the corresponding cyclobutadiene (46%) and the cyclopentadienone (10%) complexes; see: Rausch, M. D.; Genetti, R. A. J. Org. Chem. 1970, 35, 3888.
14. Hutchinson, E. J.; Kerr, W. J.; Magennis, E. J. Chem. Commun. 2002, 2262.
15. Fischer, S.; Groth, U.; Jung, M.; Schneider, A. Synlett 2002, 2023.
16. int = 0.0674, T = 120(2) K, final R indices for I > 2σ(I) R1 = 0.0537, wR2 = 0.1146 and for all data R1 = 0.1060, wR2 = 0.1375.
17. 13 ee = 98%), was followed by benzoylation, fragmentation to the primary acetylene, and Sonagashira cross-coupling with iodobenzene. See the Supporting Information.
18. Boyall, D.; López, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233.
19. (a) Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 1996, 61, 3214.
20. (b) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
21. (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091.
22. (d) Schubert, T.; Hummel, W.; Kula, M.-R.; Müller, M. Eur. J. Org. Chem. 2001, 4181.
23. (e) Li, X.; Lu, G.; Kwok, W. H.; Chan, A. S. C. J. Am. Chem. Soc. 2002, 124, 12636.