High-yield synthesis of a chiroporphyrin by hydrogen bond-directed cyclisation

Chemical Communications

Volumn , Issue 16, 1999, Pages 1597-1598

  Pérollier, Céline ^a   Pécaut, Jacques ^a   Ramasseul, René ^a   Bau, Robert ^b   Marchon, Jean Claude ^a  

^a Lab de Chimie de Coordination   (France)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; PORPHYRIN DERIVATIVE;

ARTICLE; CYCLIZATION; HYDROGEN BOND; SYNTHESIS;

EID: 0343179049     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904134f     Document Type: Article

References (18)

1. M. Veyrat, L. Fantin, S. Desmoulins, A. Petitjean, M. Mazzanti, R. Ramasseul, J.-C. Marchon and R. Bau, Bull. Soc. Chim. Fr., 1997, 134, 703.
2. C. Pérollier, J. Pécaut, R. Ramasseul and J.-C. Marchon, Bull. Soc. Chim. Fr., 1997, 134, 517.
3. M. Veyrat, O. Maury, F. Faverjon, D. E. Over, R. Ramasseul, J.-C. Marchon, I. Turowska-Tyrk and W. R. Scheldt, Angew. Chem., Int. Ed. Engl., 1994, 33, 220; C. Pérollier, J. Pécaut, R. Ramasseul and J.-C. Marchon, Inorg. Chem., 1999, in the press.
4. M. Veyrat, O. Maury, F. Faverjon, D. E. Over, R. Ramasseul, J.-C. Marchon, I. Turowska-Tyrk and W. R. Scheldt, Angew. Chem., Int. Ed. Engl., 1994, 33, 220; C. Pérollier, J. Pécaut, R. Ramasseul and J.-C. Marchon, Inorg. Chem., 1999, in the press.
5. J.-P. Simonato, J. Pécaut, W. R. Scheldt and J.-C. Marchon, Chem. Commun., 1999, 989.
6. M. Mazzanti, M. Veyrat, R. Ramasseul, J.-C. Marchon, I. Turowska-Tyrk, M. Shang and W. R. Scheldt, Inorg. Chem., 1996, 35, 3733.
7. D. Toronto, F. Sarrazin, J. Pecaut, J.-C. Marchon, M. Shang and W. R. Scheidt, Inorg. Chem., 1998, 37, 526.
8. J.-P. Simonato, J. Pécaut and J.-C. Marchon, J. Am. Chem. Soc., 1998, 120, 7363.
9. J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828.
10. C. Pérollier, Doctoral Thesis, Université Joseph Fourier, Grenoble, 1998.
11. For structurally characterised examples of strong dimerisation via complementary hydrogen bonding between urea N-H donors and amide C=O acceptors, see: F. H. Beijer, R. P. Sijbesma, H. Kooijman, A. L. Spek and E. W. Meijer, J. Am. Chem. Soc., 1998, 120, 6761.
12. For reviews of hydrogen-bonded self-assembling complexes, see: D. S. Lawrence, T. Jiang and M. Levitt, Chem. Rev., 1995, 95, 2229; M. M. Conn and J. Rebek, Jr., Chem. Rev., 1997, 97, 1467. For a previous example of macrocyclisation directed by hydrogen bonding, see: F. J. Carver, C. A. Hunter and R. J. Shannon, J. Chem. Soc., Chem. Commun., 1994, 1277.
13. For reviews of hydrogen-bonded self-assembling complexes, see: D. S. Lawrence, T. Jiang and M. Levitt, Chem. Rev., 1995, 95, 2229; M. M. Conn and J. Rebek, Jr., Chem. Rev., 1997, 97, 1467. For a previous example of macrocyclisation directed by hydrogen bonding, see: F. J. Carver, C. A. Hunter and R. J. Shannon, J. Chem. Soc., Chem. Commun., 1994, 1277.
14. For reviews of hydrogen-bonded self-assembling complexes, see: D. S. Lawrence, T. Jiang and M. Levitt, Chem. Rev., 1995, 95, 2229; M. M. Conn and J. Rebek, Jr., Chem. Rev., 1997, 97, 1467. For a previous example of macrocyclisation directed by hydrogen bonding, see: F. J. Carver, C. A. Hunter and R. J. Shannon, J. Chem. Soc., Chem. Commun., 1994, 1277.
15. For a recent review of heme biosynthesis, see: A. R. Battersby and F. J. Leeper, Top. Curr. Chem., 1998, 195, 143. For structurally characterised uroporphyrinogen derivatives, see: G. Sawitzki and H. G. von Schnering, Angew. Chem., Int. Ed. Engl., 1976, 15, 552; C. Lehmann, B. Schweizer, C. Leumann and A. Eschenmoser, Helv. Chim. Acta, 1997, 80, 1421.
16. For a recent review of heme biosynthesis, see: A. R. Battersby and F. J. Leeper, Top. Curr. Chem., 1998, 195, 143. For structurally characterised uroporphyrinogen derivatives, see: G. Sawitzki and H. G. von Schnering, Angew. Chem., Int. Ed. Engl., 1976, 15, 552; C. Lehmann, B. Schweizer, C. Leumann and A. Eschenmoser, Helv. Chim. Acta, 1997, 80, 1421.
17. For a recent review of heme biosynthesis, see: A. R. Battersby and F. J. Leeper, Top. Curr. Chem., 1998, 195, 143. For structurally characterised uroporphyrinogen derivatives, see: G. Sawitzki and H. G. von Schnering, Angew. Chem., Int. Ed. Engl., 1976, 15, 552; C. Lehmann, B. Schweizer, C. Leumann and A. Eschenmoser, Helv. Chim. Acta, 1997, 80, 1421.
18. S. Avramovici-Grisaru and S. Sarel, Nouv. J. Chim., 1982, 6, 455.