Preparation, structure and catalytic activity of copper(II) complexes of novel 4,4′-BOX ligands

Tetrahedron Letters

Volumn 51, Issue 31, 2010, Pages 4103-4106

  Frain, David ^a   Kirby, Fiona ^a   McArdle, Patrick ^a   O'Leary, Patrick ^a  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

AraBOX; Bis(oxazoline); Catalysis; Copper; Diels Alder; Molecular modelling; XyliBOX

Indexed keywords

4,4' BISOXAZOLINE LIGAND; COPPER COMPLEX; OXAZOLINE DERIVATIVE; PHENYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; STEREOCHEMISTRY; SYNTHESIS;

ALNUS;

EID: 77954029753     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.135     Document Type: Article

References (28)

1. McManus H.A., and Guiry P. J. Chem. Rev. 104 (2004) 4151-4202
2. Desimoni G., Faita G., and Jorgensen K.A. Chem. Rev. 106 (2006) 3561-3651
3. Evans D.A., Woerpel K.A., Hinman M.M., and Faul M.M. J. Am. Chem. Soc. 113 (1991) 726-728
4. Corey E.J., Imai N., and Zhang H.Y. J. Am. Chem. Soc. 113 (1991) 728-729
5. Rasappan R., Laventine D., and Reiser O. Coord. Chem. Rev. 252 (2008) 702-714
6. Fabra M.J., Fraile J.M., Herrerias C.I., Lahoz F.J., and Mayoral J.A. Chem. Commun. (2008) 5402
7. Simonelli B., Orlandi S., Benaglia M., and Pozzi G. Eur. J. Org. Chem. 2004 (2004) 2669-2673
8. Doherty S., Goodrich P., Hardacre C., Pârvulescu V., and Paun C. Adv. Synth. Catal. 350 (2008) 295-302
9. Carreiro E.P., Burke A.J., Ramalho J.P.P., and Rodrigues A.I. Tetrahedron: Asymmetry 20 (2009) 1272-1278
10. Fraile J.M., García J.I., Gissibl A., Mayoral J.A., Pires E., Reiser O., Roldán M., and Villalba I. Chem. Eur. J. 13 (2007) 8830-8839
11. Bayardon J., Holczknecht O., Pozzi G., and Sinou D. Tetrahedron: Asymmetry 17 (2006) 1568-1572
12. McDonagh C., and O'Leary P. Tetrahedron Lett. 50 (2009) 979-982
13. Qian C.T., and Wang L.C. Tetrahedron: Asymmetry 11 (2000) 2347-2357
14. Kolodziuk R., Goux-Henry C., and Sinou D. Tetrahedron: Asymmetry 18 (2007) 2782-2786
15. Phomkeona K., Takemoto T., Ishima Y., Shibatomi K., Iwasa S., and Nishiyama H. Tetrahedron 64 (2008) 1813-1822
16. Barroso S., Blay G., Al-Midfa L., Munoz M.C., and Pedro J.R. J. Org. Chem. 73 (2008) 6389-6392
17. O'Leary P., Krosveld N.P., De Jong K.P., van Koten G., and Gebbink R. Tetrahedron Lett. 45 (2004) 3177-3180
18. Matsumoto K., Jitsukawa K., and Masuda H. Tetrahedron Lett. 46 (2005) 5687-5690
19. McGarrigle E.M., and Gilheany D.G. Chem. Rev. 105 (2005) 1563-1602
20. Kato T., Marubayashi K., Takizawa S., and Sasai H. Tetrahedron: Asymmetry 15 (2004) 3693-3697
21. Kanemasa S., Adachi K., Yamamoto H., and Wada E. Bull. Chem. Soc. Jpn. 73 (2000) 681
22. Frain D., Kirby F., McArdle P., and O'Leary P. Synlett (2009) 1261-1264
23. 2 (pet. ether/EtOAc; 75:25) to yield 9 (310 mg, 79%).
24. D +24.1 (c 0.7, MeCN, 23 °C).
25. Crystallographic data (excluding structure factors) for the structure reported in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 758186. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: (internat.) +44 1223/336-033; e-mail: deposit@ccdc.cam.ac.uk].
26. 2 for 90 min at rt. To this stirring catalyst was added 1-(trans-crotonoyl)-2-oxazolidinone (51 mg, 0.33 mmol) and freshly distilled cyclopentadiene (0.10 mL, 1.21 mmol). The reaction proceeded for 16 h. A mixture of endo and exo products was isolated as an oil. The reaction resulted in 60% conversion with an endo/exo ratio of 70:30. The crude mixture was then purified by column chromatography (pet./EtOAc, 3:2) affording a mixture of endo and exo products as a colourless oil, from which the enantiomeric excess (ee) of the endo diastereomer was found to be 44% (S), as measured on the purified product using chiral HPLC (CHIRACEL OD, 254 nm, hexane/iso-propyl alcohol, 98:2, 1.0 mL/min), t(S) 22.5, t(R) 28.5.
27. Takacs J.M., Quincy D.A., Shay W., Jones B.E., and Ross C.R. Tetrahedron: Asymmetry 8 (1997) 3079-3087
28. Maruoka K., Imoto H., and Yamamoto H. J. Am. Chem. Soc. 116 (2002) 12115-12116