Asymmetric synthesis of cyclic ethers by rearrangement of oxonium ylides generated from chiral copper carbenoids

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 97-100

  Clark, J Stephen ^a   Fretwell, Mark ^a   Whitlock, Gavin A ^a   Burns, Christopher J ^b   Fox, David N A ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; ETHER DERIVATIVE; METAL COMPLEX;

ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0031963326     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10441-5     Document Type: Article

References (22)

1. (a) Padwa, A.; Hornbuckle, S.F. Chem. Rev. 1991, 91, 263.
2. (b) Ye T.; McKervey, M.A. Chem. Rev. 1994, 94, 1091.
3. (c) Doyle, M.P. In Comprehensive organometallic Chemistry II; Hegedus, L.S. Ed.; Pergamon Press: Oxford, 1995; Vol. 12, Chapter 5.1, pp 421-468.
4. (a) Clark, J.S. Tetrahedron Lett. 1992, 33, 6193.
5. (b) Clark, J.S.; Krowiak, S.A.; Street, L.J. Tetrahedron Lett. 1993, 34, 4385.
6. (c) Clark, J.S.; Whitlock, G.A. Tetrahedron Lett. 1994, 35, 6381.
7. (d) Clark, J.S.; Dossetter, A.G.; Whittingham, W.G. Tetrahedron Lett. 1996, 37, 5605.
8. West F.G., Naidu B.N., Tester R.W. J. Org. Chem. 59:1994;6892.
9. Nozaki H., Takaya H., Moriuti S., Noyori R. Tetrahedron. 24:1968;3655.
10. Ito K., Yoshitake M., Katsuki T. Heterocycles. 42:1996;305.
11. (a) McCarthy, N.; McKervey, M.A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M.P. Tetrahedron Lett. 1992, 33, 5983.
12. (b) Pierson, N.; Fernández-Garciá, C.; McKervey, M.A. Tetrahedron Lett. 1997, 38, 4705.
13. Doyle M.P., Ene D.G., Forbes D.C., Tedrow J.S. Tetrahedron Lett. 38:1997;4367.
14. Doyle M.P. Aldrichimica Acta. 29:1996;3.
15. Other classes of ligands that were screened included bisoxazolines, chiral 1,3-diketones derived from camphor and diimines produced by condensation of 2,2′-diamino-1,1′-binaphthalene with various aldehydes.
16. Li, Z.; Conser, K.R.; Jacobsen, E.N. J. Am. Chem. Soc. 1993, 115, 5326. Li, Z.; Quan, R.W.; Jacobsen, E.N. J. Am. Chem. Soc. 1995, 117, 5889.
17. Li, Z.; Conser, K.R.; Jacobsen, E.N. J. Am. Chem. Soc. 1993, 115, 5326. Li, Z.; Quan, R.W.; Jacobsen, E.N. J. Am. Chem. Soc. 1995, 117, 5889.
18. Use of copper complexes of diimines 1b-j ( ) as pre-catalysts for the cyclisation of the α-diazo ketone 2a afforded samples of the cyclic ether 3a with enantiomeric excesses of less than 32% ( ).
19. Trost B.M., Belletire J.L., Godleski S., McDougal P.G., Balkovec J.M., Baldwin J.J., Christy M.E., Ponticello G.S., Varga S.L., Springer J.P. J. Org. Chem. 51:1986;2370.
20. 1H NMR spectrum.
21. The optimum reaction time was found to be approximately 10 minutes. Prolonging the reaction time to 1-2 hours resulted in a 15-30% (relative) erosion in enantiomeric purity of the product.
22. For a review of 'chirality transfer' during sigmatropic rearrangements, see: Hill, R.K. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press: 1983; Vol. 3, Chapter 8, pp 503-572.