Isocyanates - Part 3. Synthesis of carbamates by DMAP-catalyzed reaction of amines with di-tert-butyldicarbonate and alcohols

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5861-5864

  Knölker, Hans Joachim ^a   Braxmeier, Tobias ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; ALCOHOL DERIVATIVE; ALIPHATIC AMINE; AMINOPYRIDINE DERIVATIVE; AROMATIC AMINE; CARBAMIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; INFRARED SPECTROMETRY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS;

EID: 0030581330     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01248-8     Document Type: Article

References (20)

1. 1. U. Petersen in Methoden Org. Chem. (Houben-Weyl), 4th ed., Vol. E4, 1983, p. 142.
2. 2. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991, Chap. 7, p. 309. P. J. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994, Chap. 6, p. 185.
3. 2. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991, Chap. 7, p. 309. P. J. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994, Chap. 6, p. 185.
4. 3. S. Ozaki, Chem. Rev. 1972, 72, 457. K. Findeisen, K. König, R. Sundermann in Methoden Org. Chem. (Houben-Weyl), 4th ed., Vol. E4, 1983, p. 738.
5. 3. S. Ozaki, Chem. Rev. 1972, 72, 457. K. Findeisen, K. König, R. Sundermann in Methoden Org. Chem. (Houben-Weyl), 4th ed., Vol. E4, 1983, p. 738.
6. 4. For some newer methods for the synthesis of carbamates, see: A. Benalil, P. Roby, B. Carboni, M. Vaultier, Synthesis 1991, 787. W. D. McGhee, Y. Pan, D. P. Riley, J. Chem. Soc. Chem. Commun. 1994, 699. E. Engeles, A. Santillán, I. Martínez, A. Ramírez, E. Moreno, Synth. Commun. 1994, 24, 2441. T. Patonay, L. Hegedüs, F. Mogyoródi, L. Zolnai, Synth. Commun. 1994, 24, 2507. W. McGhee, D. Riley, K. Christ, Y. Pan, B. Parnas, J. Org. Chem. 1995, 60, 2820. P. Wehman, P. C. J. Kramer, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1996, 217.
7. 4. For some newer methods for the synthesis of carbamates, see: A. Benalil, P. Roby, B. Carboni, M. Vaultier, Synthesis 1991, 787. W. D. McGhee, Y. Pan, D. P. Riley, J. Chem. Soc. Chem. Commun. 1994, 699. E. Engeles, A. Santillán, I. Martínez, A. Ramírez, E. Moreno, Synth. Commun. 1994, 24, 2441. T. Patonay, L. Hegedüs, F. Mogyoródi, L. Zolnai, Synth. Commun. 1994, 24, 2507. W. McGhee, D. Riley, K. Christ, Y. Pan, B. Parnas, J. Org. Chem. 1995, 60, 2820. P. Wehman, P. C. J. Kramer, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1996, 217.
8. 4. For some newer methods for the synthesis of carbamates, see: A. Benalil, P. Roby, B. Carboni, M. Vaultier, Synthesis 1991, 787. W. D. McGhee, Y. Pan, D. P. Riley, J. Chem. Soc. Chem. Commun. 1994, 699. E. Engeles, A. Santillán, I. Martínez, A. Ramírez, E. Moreno, Synth. Commun. 1994, 24, 2441. T. Patonay, L. Hegedüs, F. Mogyoródi, L. Zolnai, Synth. Commun. 1994, 24, 2507. W. McGhee, D. Riley, K. Christ, Y. Pan, B. Parnas, J. Org. Chem. 1995, 60, 2820. P. Wehman, P. C. J. Kramer, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1996, 217.
9. 4. For some newer methods for the synthesis of carbamates, see: A. Benalil, P. Roby, B. Carboni, M. Vaultier, Synthesis 1991, 787. W. D. McGhee, Y. Pan, D. P. Riley, J. Chem. Soc. Chem. Commun. 1994, 699. E. Engeles, A. Santillán, I. Martínez, A. Ramírez, E. Moreno, Synth. Commun. 1994, 24, 2441. T. Patonay, L. Hegedüs, F. Mogyoródi, L. Zolnai, Synth. Commun. 1994, 24, 2507. W. McGhee, D. Riley, K. Christ, Y. Pan, B. Parnas, J. Org. Chem. 1995, 60, 2820. P. Wehman, P. C. J. Kramer, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1996, 217.
10. 4. For some newer methods for the synthesis of carbamates, see: A. Benalil, P. Roby, B. Carboni, M. Vaultier, Synthesis 1991, 787. W. D. McGhee, Y. Pan, D. P. Riley, J. Chem. Soc. Chem. Commun. 1994, 699. E. Engeles, A. Santillán, I. Martínez, A. Ramírez, E. Moreno, Synth. Commun. 1994, 24, 2441. T. Patonay, L. Hegedüs, F. Mogyoródi, L. Zolnai, Synth. Commun. 1994, 24, 2507. W. McGhee, D. Riley, K. Christ, Y. Pan, B. Parnas, J. Org. Chem. 1995, 60, 2820. P. Wehman, P. C. J. Kramer, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1996, 217.
11. 4. For some newer methods for the synthesis of carbamates, see: A. Benalil, P. Roby, B. Carboni, M. Vaultier, Synthesis 1991, 787. W. D. McGhee, Y. Pan, D. P. Riley, J. Chem. Soc. Chem. Commun. 1994, 699. E. Engeles, A. Santillán, I. Martínez, A. Ramírez, E. Moreno, Synth. Commun. 1994, 24, 2441. T. Patonay, L. Hegedüs, F. Mogyoródi, L. Zolnai, Synth. Commun. 1994, 24, 2507. W. McGhee, D. Riley, K. Christ, Y. Pan, B. Parnas, J. Org. Chem. 1995, 60, 2820. P. Wehman, P. C. J. Kramer, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1996, 217.
12. 5. H.-J. Knölker, T. Braxmeier, G. Schlechtingen, German patent application P 19526081.3, 1995.
13. 6. H.-J. Knölker, T. Braxmeier, G. Schlechtingen, Angew. Chem. 1995, 107, 2746; Angew. Chem. Int. Ed. Engl. 1995, 34, 2497.
14. 6. H.-J. Knölker, T. Braxmeier, G. Schlechtingen, Angew. Chem. 1995, 107, 2746; Angew. Chem. Int. Ed. Engl. 1995, 34, 2497.
15. 7. Part 2: H.-J. Knölker, T. Braxmeier, G. Schlechtingen, Synlett 1996, 502.
16. 3): 198.1494, found: 198.1483.
17. 9. L. Grehn, U. Ragnarsson, Angew. Chem. 1985, 97, 519; Angew. Chem. Int. Ed. Engl. 1985, 24, 510. A. Könnecke, L. Grehn, U. Ragnarsson, Tetrahedron Lett. 1990, 31, 2697.
18. 9. L. Grehn, U. Ragnarsson, Angew. Chem. 1985, 97, 519; Angew. Chem. Int. Ed. Engl. 1985, 24, 510. A. Könnecke, L. Grehn, U. Ragnarsson, Tetrahedron Lett. 1990, 31, 2697.
19. 9. L. Grehn, U. Ragnarsson, Angew. Chem. 1985, 97, 519; Angew. Chem. Int. Ed. Engl. 1985, 24, 510. A. Könnecke, L. Grehn, U. Ragnarsson, Tetrahedron Lett. 1990, 31, 2697.
20. 10. H. Shanan-Atidi, K. H. Bar-Eli, J. Phys. Chem. 1970, 74, 961.