Synthesis of an enantiomerically pure building block for the synthesis of hydroporphyrins

European Journal of Organic Chemistry

Volumn , Issue 2, 2007, Pages 249-257

  Adukpo, Genevieve Etornam ^a,b   Borrmann, Tobias ^a   Manski, René ^a   Sáez Díaz, Rosa I ^a,c   Stohrer, Wolf Dieter ^a   Montforts, Franz Peter ^a  

^a UNIVERSITY OF BREMEN   (Germany)

^b UNIVERSITY OF CAPE COAST   (Ghana)

^c DALHOUSIE UNIVERSITY   (Canada)

Author keywords

Chiral resolution; Circular dichroism; Hydroporphyrins; Nitrogen heterocycles

Indexed keywords

EID: 33846516485     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600656     Document Type: Article

References (39)

1. a) D. Dolphin, The Porphyrins, Academic Press, New York, 1978-1979, vol. 1-7;
2. b) K. M. Kadish, K. M. Smith, R. Guilard, The Porphyrin Handbook, Academic Press, New York, 2000, vol. 1-10,
3. 2003, vol. 11-20.
4. P. H. Hynninen, Chemistry of Chlorophylls: Modifications, in: H. Scheer, Chlorophylls, CRC Press, Boca Raton, 1991, p. 145.
5. 12, Wiley, New York, 1982, vol. I and II;
6. 12-Proteins, Wiley-VCH, Weinheim, 1998 ;
7. c) A. Eschenmoser, Angew. Chem. 1988, 100, 5-40.
8. a) F.-P. Montforts, B. Gerlach, F. Höper, Chem. Rev. 1994, 94, 327-347;
9. b) B. Kräutler, Chimia 1987, 41, 277-292;
10. c) F.-P. Montforts, M. Glasenapp-Breiling, The Synthesis of Chlorins, Bacteriochlorins, Isobacteriochlorins and Higher Reduced Porphyrins, in: G. W. Gribble, T. L. Gilchrist, Progress in Heterocyclic Chemistry, Pergamon, Elsevier Science Ltd., 1998, vol. 10, p. 1;
11. d) F.-P. Montforts, M. Glasenapp-Breiling, Naturally Occurring Cyclic Tetrapyrroles, in: W. Herz, H. Falk, G. W. Kirby, Progress in the Chemistry of Organic Natural Products, Springer, Wien, New York, 2002, 84, p. 1.
12. F.-P. Montforts, M. Glasenapp-Breiling, D. Kusch, Houben-Weyl Methods of Organic Chemistry, E. Schaumann, Thieme, Stuttgart, New York, 1998, vol. E9 d, p. 577.
13. a) R. J. Snow, C. J. R. Fookes, A. R. Battersby, J. Chem. Soc., Chem. Commun. 1981, 524-526;
14. b) S. P. D. Turner, M. H. Block, Z. C. Sheng, S. C. Zimmermann, A. R. Battersby, J. Chem. Soc., Chem. Commun. 1985, 583-585;
15. c) C. J. Dutton, C. J. R. Fookes, A. R. Battersby, J. Chem. Soc., Chem. Commun. 1983, 1237-1238;
16. d) A. R. Battersby, S. W. Westwood, J. Chem. Soc., Perkin Trans. 1 1987, 1679-1687;
17. e) J. Micklefield, M. Beckmannn, R. L. Hackman, M. H. Block, F. J. Leeper, A. R. Battersby, J. Chem. Soc., Perkin Trans. 1 1997, 2123-2138.
18. a) A. Eschenmoser, C. E. Winter, Science 1977, 196, 1410-1420;
19. b) F.-P. Montforts, S. Ofner, V. Rasetti, A. Eschenmoser, W.-D. Woggon, K. Jones, A. R. Battersby, Angew. Chem. Int. Ed. Engl. 1979, 18, 675-677;
20. c) A. Eschenmoser, Nova Acta Leopoldina 1982, 55, 5.
21. a) T. G. Minehan, Y. Kishi, Angew. Chem. 1999, 111, 972-975;
22. b) T. G. Mineham, Y. Kishi, Tetrahedron Lett. 1997, 38, 6811-6814.
23. a) M. Taniguchi, D. Ra, G. Mo, T. Balasubramanian, J. S. Lindsey, J. Org. Chem. 2001, 66, 7342-7354;
24. b) H.-J. Kim, J. S. Lindsey, J. Org. Chem. 2005, 70, 5475-5486.
25. a) F.-P. Montforts, Angew. Chem. 1981, 95, 795-796;
26. b) F.-P. Montforts, U. M. Schwartz, Angew. Chem. 1985, 97, 767-768;
27. c) F.-P. Montforts, F. Romanowski, J. W. Bats, Tetrahedron Lett. 1992, 33, 765-768;
28. d) D. Kusch, E. Töllner, A. Lincke, F.-P. Montforts, Angew. Chem. 1995, 107, 874-877.
29. K. Harke, H. Roeber, R. Matusch, Chem. Ber. 1975, 108, 3246-3261.
30. a) T. W. Greene, P. G. M. Wuts, Protecting Groups in Organic Synthesis, Wiley, New York, 1999, p. 3;
31. b) B. D. Gray, P. W. Jeffs, J. Chem. Soc., Chem. Commun. 1987, 1329-1330;
32. c) S. D. Bull, S. G. Davies, G. Fenton, A. W. Mulvaney, R. S. Prasad, A. D. Smith, J. Chem. Soc., Perkin Trans. 1 2000, 3765-3774.
33. a) J. Clayden, F. E. Knowles, C. J. Menet, Tetrahedron Lett. 2003, 44, 3397-3400;
34. b) S. D. Bull, S. G. Davies, P. M. Kelly, M. Gianotti, A. D. Smith, J. Chem. Soc., Perkin Trans. 1 2001, 3106-3111;
35. c) R. A. Bragg, J. Clayden, C. J. Menet, Tetrahedron Lett. 2002, 43, 1955-1959.
36. a) R. S. Varma, D. Kumar, Org. Lett. 1999, 1, 697-700;
37. b) M. P. Cava, M. I. Levinson, Tetrahedron 1985, 41, 5061-5087.
38. M. Roth, P. Dubs, E. Götschi, A. Eschenmoser, Helv. Chim. Acta 1971, 54, 710-734.
39. A. Eschenmoser, C. Winter, Science 1977, 196, 1410-1420.