Synthesis of polymer-bound Fischer chromium alkoxy and aminocarbene complexes

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3635-3638

  Maiorana, Stefano ^a   Seneci, Pierfausto ^b   Rossi, Tino ^b   Baldoli, Clara ^a   Ciraco', Manuela ^a   De Magistris, Elisabetta ^b   Licandro, Emanuela ^a   Papagni, Antonio ^a   Provera, Stefano ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b GLAXOSMITHKLINE   (United States)

Author keywords

Phosphino chromium carbonyls; Polymer bound Fischer carbenes; Solid phase synthesis

Indexed keywords

AMINE; AMINOCARBENE; CARBOXYL GROUP; CHROMIUM DERIVATIVE; CHROMIUM PENTACARBONYL CARBENE; LIGAND; POLYMER; RESIN; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033617345     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00521-3     Document Type: Article

References (25)

1. 1. For reviews of Fischer carbene complexes see: Wulff, W. D.; Organometallics 1998, 17, 3116-3134; L. S.Hegedus, Tetrahedron 1997, 53, 4105-4128; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, A. W., Stone F. G. A.; Wilkinson, G. Eds.; Pergamon: Oxford, 1995, Vol. 12, pp 469-547; Hegedus, L. S. ibid Vol 12, pp 549-576; Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587-608.
2. 1. For reviews of Fischer carbene complexes see: Wulff, W. D.; Organometallics 1998, 17, 3116-3134; L. S. Hegedus, Tetrahedron 1997, 53, 4105-4128; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, A. W., Stone F. G. A.; Wilkinson, G. Eds.; Pergamon: Oxford, 1995, Vol. 12, pp 469-547; Hegedus, L. S. ibid Vol 12, pp 549-576; Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587-608.
3. 1. For reviews of Fischer carbene complexes see: Wulff, W. D.; Organometallics 1998, 17, 3116-3134; L. S.Hegedus, Tetrahedron 1997, 53, 4105-4128; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, A. W., Stone F. G. A.; Wilkinson, G. Eds.; Pergamon: Oxford, 1995, Vol. 12, pp 469-547; Hegedus, L. S. ibid Vol 12, pp 549-576; Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587-608.
4. 1. For reviews of Fischer carbene complexes see: Wulff, W. D.; Organometallics 1998, 17, 3116-3134; L. S.Hegedus, Tetrahedron 1997, 53, 4105-4128; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, A. W., Stone F. G. A.; Wilkinson, G. Eds.; Pergamon: Oxford, 1995, Vol. 12, pp 469-547; Hegedus, L. S. ibid Vol 12, pp 549-576; Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587-608.
5. 1. For reviews of Fischer carbene complexes see: Wulff, W. D.; Organometallics 1998, 17, 3116-3134; L. S.Hegedus, Tetrahedron 1997, 53, 4105-4128; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, A. W., Stone F. G. A.; Wilkinson, G. Eds.; Pergamon: Oxford, 1995, Vol. 12, pp 469-547; Hegedus, L. S. ibid Vol 12, pp 549-576; Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587-608.
6. 2. Hermkens, P. H. H.; Ottenheijm, C.J; Rees, D.C Tetrahedron 1997, 53, 5643-5678; Guest, J. W. Ed Chem.Rev. 1997, Vol 97; Thompson, L. A.; Ellman, J.A. Chem. Rev. 1996, 96, 555-600.
7. 2. Hermkens, P. H. H.; Ottenheijm, C.J; Rees, D.C Tetrahedron 1997, 53, 5643-5678; Guest, J. W. Ed Chem. Rev. 1997, Vol 97; Thompson, L. A.; Ellman, J.A. Chem. Rev. 1996, 96, 555-600.
8. 2. Hermkens, P. H. H.; Ottenheijm, C.J; Rees, D.C Tetrahedron 1997, 53, 5643-5678; Guest, J. W. Ed Chem.Rev. 1997, Vol 97; Thompson, L. A.; Ellman, J.A. Chem. Rev. 1996, 96, 555-600.
9. 3 complexes. Semmelhack, M. F.; Hilt, G.; Colley, J. H.; Tetrahedron Lett. 1998, 39, 7683-7686. Gibson has more recently used chromium tricarbonyl complexes as tracelesslinkers: Gibson (née Thomas), S. E.; Hales, J. N.; Peplow, M.A. Tetrahedron Lett. 1999, 40, 1417-1418
10. 3 complexes. Semmelhack, M. F.; Hilt, G.; Colley, J. H.; TetrahedronLett. 1998, 39, 7683-7686. Gibson has more recently used chromium tricarbonyl complexes as traceless linkers: Gibson (née Thomas), S. E.; Hales, J. N.; Peplow, M.A. Tetrahedron Lett. 1999, 40, 1417-1418
11. 4. Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Hughes, I Tetrahedron Lett. 1996, 37, 7595-7598; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Hu, Y.; Porco, J. A. Jr., Labadie, J. W.; Gooding, O.W.; Trost, B. M. J. Org. Chem. 1998, 63, 4518-4521.
12. 4. Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Hughes, I Tetrahedron Lett. 1996, 37, 7595-7598; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Hu, Y.; Porco, J. A. Jr., Labadie, J. W.; Gooding, O.W.; Trost, B. M. J. Org. Chem. 1998, 63, 4518-4521.
13. 4. Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Hughes, I Tetrahedron Lett. 1996, 37, 7595-7598; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Hu, Y.; Porco, J. A. Jr., Labadie, J. W.; Gooding, O.W.; Trost, B. M. J. Org. Chem. 1998, 63, 4518-4521.
14. 4. Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Hughes, I Tetrahedron Lett. 1996, 37, 7595-7598; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Hu, Y.; Porco, J. A. Jr., Labadie, J. W.; Gooding, O.W.; Trost, B. M. J. Org. Chem. 1998, 63, 4518-4521.
15. 5. a) Fischer, E. O.; Fischer, H Chem. Ber. 1974, 107, 657. b) Wulff, W. D.; Xu, Y. C. J. Org. Chem. 1987, 52, 3263-3275. c) Fischer, E. O.; Auman, R. Chem. Ber. 1969, 102, 1495-1503.
16. 5. a) Fischer, E. O.; Fischer, H Chem. Ber. 1974, 107, 657. b) Wulff, W. D.; Xu, Y. C. J. Org. Chem. 1987, 52, 3263-3275. c) Fischer, E. O.; Auman, R. Chem. Ber. 1969, 102, 1495-1503.
17. 5. a) Fischer, E. O.; Fischer, H Chem. Ber. 1974, 107, 657. b) Wulff, W. D.; Xu, Y. C. J. Org. Chem. 1987, 52, 3263-3275. c) Fischer, E. O.; Auman, R. Chem. Ber. 1969, 102, 1495-1503.
18. 6 (80°C in DMF for 10h).
19. 7. Resin 1 was obtained as reported by M. Bernard, W. T. Ford, J. Org. Chem. 1983, 48, 326-332, starting from PL-PBS, (2 mmol/g), Polymer Laboratories Inc.
20. 3). Compound 3c proved to be the least stable of the polymer-bound carbenes, which could account for the low reaction yield.
21. 2); 8.25 (bs, 1H, NH).
22. 13
23. 11. The Fmoc group was removed by treating resins 6a,b (120 mg,0.66 mmol/g) and 7a,b (120 mg, 0.38 mmol/g) with an excess of 20% solution of piperidine in DMF at room temperature for 1h.
24. -1):. 8a, 2055; 1971; 1916; 1740. 8b, 2055; 1972; 1916; 1740. 9a, 2053; 1970; 1928; 1741. 9b, 2053; 1970; 1923; 1741.
25. 13. Bunin, B. A. The Combinatorial Index Academic Press. S. Diego, 1998, 5, 219.