One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc

Tetrahedron Letters

Volumn 44, Issue 51, 2003, Pages 9127-9129

  Vatèle, Jean Michel ^a  

^a CPE LYON   (France)

Author keywords

Amines; Carbamates; Deprotection; Iodine; Zinc

Indexed keywords

AMINE; AROMATIC COMPOUND; CARBAMIC ACID DERIVATIVE; CARBONYL DERIVATIVE; DIMETHYL ETHER; ETHER DERIVATIVE; INDOLE DERIVATIVE; IODINE; METHANOL; SULFIDE; ZINC;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; MOLECULAR INTERACTION; POWDER;

EID: 0344413534     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.058     Document Type: Article

References (19)

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2. Vatèle J.-M. Synlett. 2001;1989-1991.
3. Vatèle J.-M. Synlett. 2002;507-509.
4. Vatèle J.-M. Tetrahedron. 58:2002;5689-5698.
5. Ho T.L. Heterocyclic Fragmentation of Organic Molecules. 1993;49 Wiley, New York.
6. For a good example of this fragmentation, see the deprotection of trichloroethylcarbamates: Mineno T., Choi S.-R., Avery M.A. Synlett. 2002;883-886. and references cited therein.
7. Rieke R.D., Sell M.S. Rakta G.S., Rakta P.E. Handbook of Grignard Reagents. 1996;53 Silverman, Marcel Dekker.
8. Activation of zinc by iodine is precedented, see for example: (a) Palmer, M. H.; Reid, J. A. J. Chem. Soc. 1960, 931-938; (b) Huo, S. Org. Lett. 2003, 5, 423-425.
9. Activation of zinc by iodine is precedented, see for example: (a) Palmer, M. H.; Reid, J. A. J. Chem. Soc. 1960, 931-938; (b) Huo, S. Org. Lett. 2003, 5, 423-425.
10. Garst J.F., Ungvary F. Richey H.G. Grignard Reagents: New Developments. 7:2000;185 John Wiley.
11. Prenyl carbamates 1a-k were prepared from the corresponding amines and prenyl p-nitrophenyl carbonate in the presence of a catalytic amount of DMAP.
12. All new compounds gave satisfactory physical and analytical data.
13. 3, 50 MHz): 14.4, 28.9, 29.2, 52.2, 54.2, 171.0.
14. For a study of the iodine oxidation of methionine, see: Young P.R., Hsieh L.S. J. Am. Chem. Soc. 100:1978;7121-7122.
15. This Zn-mediated intramolecular transesterification is reminiscent of the intramolecular cleavage of phosphodiesters catalyzed by Zn(II) coordinated to amines: (a) Mollenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75-86; (b) Bonfà, L.; Gatos, M.; Mancin, F.; Teulla, P.; Tonellato, U. Inorg. Chem. 2003, 42, 3943-3949.
16. This Zn-mediated intramolecular transesterification is reminiscent of the intramolecular cleavage of phosphodiesters catalyzed by Zn(II) coordinated to amines: (a) Mollenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75-86; (b) Bonfà, L.; Gatos, M.; Mancin, F.; Teulla, P.; Tonellato, U. Inorg. Chem. 2003, 42, 3943-3949.
17. Until now, only one method to deprotect the N-Preoc group has been described: Lemaire-Audoire, S.; Savignac, M.; Pourcelot, G.; Genêt, J.-P. ; Bernard, J.-M. J. Mol. Cat. A: Chem. 1997, 116, 247-258.
18. Aldrich Chemical Company, zinc dust <10 micron Catalog # 20,998-8.
19. Rachele J.R. J. Org. Chem. 28:1963;2898.