The Lindlar catalyst revitalized: A highly chemoselective method for the direct conversion of azides to N-(tert-butoxycarbonyl)amines

European Journal of Organic Chemistry

Volumn , Issue 22, 2002, Pages 3740-3743

  Ganapati Reddy, P ^a   Verabhadra Pratap, T ^a   Kishore Kumar, G D ^a   Mohanty, Subhendu K ^a   Baskaran, Sundarababu ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Azides; Chemoselectivity; Chiral ligands; Lindlar catalyst; Reduction; Synthetic methods

Indexed keywords

AMINE; AZIDE; N (TERT BUTOXYCARBONYL)AMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036857836     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz H. Yamamoto) Springer, Heidelberg, 1999.
2. [2a] I. Ojima, Catalytic Asymmetric Synthesis, 2nd ed. VCH, Weinheim 2000.
3. [2b] R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York 1994.
4. [2c] H. Brunner, W. Zettlmeier, Handbook for Enantioselective Catalysis, VCH, Weinheim 1993.
5. [2d] M. Beller, C. Bolm, Transition, Metals for Organic Synthesis, Wiley-VCH, Weinheim, 1998.
6. [3a] L. E. Martinez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897-5898.
7. [3b] J. F. Larrow, S. E. Schaus, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 7420-7421.
8. [4a] Y. Gao, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 7538-7539.
9. [4b] H.-T. Chang, K. B. Sharpless, Tetrahedron Lett. 1996, 37, 3219-3222.
10. B. B. Lohray, Y. Gao, K. B. Sharpless, Tetrahedron Lett. 1989, 30, 2623-2626.
11. [6a] D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
12. [6b] F. Fache, E. Schulz, M. L. Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2232.
13. D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627.
14. D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627.
15. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley: New York, 1999.
16. [9a] S. Saito, H. Nakajima, M. Inaba, T. Moriwake, Tetrahedron Lett. 1989, 30, 837-838.
17. [9b] H. Kotsuki, T. Ohishi, T. Araki, Tetrahedron Lett. 1997, 38, 2129-2132.
18. [10a] C. A. M. Afonso, Tetrahedron Lett. 1995, 36, 8857-8858.
19. [10b] X. Ariza, O. Pineda, F. Urpi, J. Vilarrasa, Tetrahedron Lett. 2001, 42, 4995-4999.
20. [11a] D. A. Nugiel, K. Jacobs, T. Worley, M. Patel, R. F. Kaltenbach, D. T. Meyer, P. K. Jadhav, G. V. De Lucca, T. E. Smyser, R. M. Klabe, L. T. Bacheler, M. M. Rayner, S. P. Seitz, J. Med. Chem. 1996, 39, 2156-2169.
21. [11b] J. Hulten, N. M. Bonham, U. Nillroth, T. Hansson, G. Zuccarello, A. Bouzide, J. Aqvist, B. Classon, U. H. Danielson, A. Karlen, I. Kvarnstrom, B. Samuelsson, A. Hallberg, J. Med. Chem. 1997, 40, 885-897.
22. [12a] Lindlar catalyst mediated selective reduction of azides to primary amines, in the presence of double bonds and benzyl ether, has been reported previously: E. J. Corey, K. C. Nicolaou, R. D. Balanson, Y. Machida, Synthesis 1975, 590-591.
23. [12b] Reduction of azide to amine without affecting the N-Cbz protecting group has been observed: D. C. Horwell, J. Hughes, J. C. Hunter, M. C. Pritchard, R. S. Richardson, E. Roberts, G. N. Woodruff, J. Med. Chem. 1991, 34, 404-414.
24. [12c] However, hydrogenolysis of na N-Cbz protecting group has been reported with Lindlar catalyst: A. K. Ghosh, K. Krishnan, Tetrahedron Lett. 1988, 39, 947-948.
25. Different batches of Lindlar catalyst procured from different sources (Merck and Aldrich) were found to give the same results.
26. 2O reagent system: M. Sakaitani, K. Hori, Y. Ohfune, Tetrahedron Lett. 1988, 29, 2983-2984.
27. B. B. Lohray, S. Baskaran, B. S. Rao, B. Y. Reddy, I. N. Rao, Tetrahedron Lett. 1999, 40, 4855-4856.
28. Several modified palladium catalysts have been reported for the selective hydrogenation/hydrogenolysis of N-Cbz, benzyl ester and azide in the presence of aliphatic and phenolic O-benzyl protecting groups.
29. [16a] J. S. Bajwa, Tetrahedron Lett. 1992, 33, 2299-2302.
30. [16b] H. Sajiki, H. Kuno, K. Hirota, Tetrahedron Lett. 1997, 38, 399-402.
31. [16c] Y. Shi, L. F. Peng, Y. Kishi, J. Org. Chem. 1997, 62, 05666-5667.
32. [16d] H. Sajiki, K. Hirota, Tetrahedron 1998, 54, 13981-13996.
33. A. Scheurer, P. Mosset, R. W. Saalfrank, Tetrahedron: Asymmetry 1997, 8, 1243-1251.
34. B. B. Lohray, S. Baskaran, B. S. Rao, B. Mallesham, K. S. N. Bharath, B. Y. Reddy, S. Venkateswarlu, A. K. Sadhukhan, M. S. Kumar. H. M. Sarnaik, Bioorg. Med. Chem. Lett. 1998, 8, 525-528.
35. K. Hattori, H. Sajiki, K. Hirota, Tetrahedron Lett. 2000, 41, 5711-5714.
36. B. B. Lohray, S. Baskaran, B. Y. Reddy, K. S. Rao, Tetrahedron Lett. 1998, 39, 6555-6556.