A new facile method for the chemoselective reductive transformation of azides to N-(tert-butoxycarbonyl)amines

Tetrahedron Letters

Volumn 38, Issue 12, 1997, Pages 2129-2132

  Kotsuki, Hiyoshizo ^a   Ohishi, Takeshi ^a   Araki, Tomohiro ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZIDE; HETEROCYCLIC AMINE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; REDUCTION;

EID: 0031585032     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00324-9     Document Type: Article

References (33)

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2. 1. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297-368; Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; VCH: New York, 1989, 409-410; Gilchrist, T. L. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds., Pergamon Press: Oxford, 1991, 8, 383-386.
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6. 2. For the most recent examples, see: Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254-2256; Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. ibid. 1995, 60, 7682-7683; Tamami, B.; Lakouraj, M. M. Syn. Commun. 1995, 25, 3089-3096; Huang, Y.; Zhang, Y. ibid. 1996, 26, 2911-2915; Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567-2570; Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. ibid. 1995, 36, 7313-7314; Goulaouic-Dubois, C.; Hesse, M. ibid. 1995, 36, 7427-7430; Salunkhe, A. M.; Brown, H. C. ibid. 1995, 36, 7987-7990; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. ibid. 1996, 37, 4559-4560; Cho, S.-D.; Choi, W.-Y.; Lee, S.-G.; Yoon, Y.-J.; Shin, S. C. ibid. 1996, 37, 7059-7060; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193-1194.
7. 2. For the most recent examples, see: Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254-2256; Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. ibid. 1995, 60, 7682-7683; Tamami, B.; Lakouraj, M. M. Syn. Commun. 1995, 25, 3089-3096; Huang, Y.; Zhang, Y. ibid. 1996, 26, 2911-2915; Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567-2570; Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. ibid. 1995, 36, 7313-7314; Goulaouic-Dubois, C.; Hesse, M. ibid. 1995, 36, 7427-7430; Salunkhe, A. M.; Brown, H. C. ibid. 1995, 36, 7987-7990; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. ibid. 1996, 37, 4559-4560; Cho, S.-D.; Choi, W.-Y.; Lee, S.-G.; Yoon, Y.-J.; Shin, S. C. ibid. 1996, 37, 7059-7060; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193-1194.
8. 2. For the most recent examples, see: Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254-2256; Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. ibid. 1995, 60, 7682-7683; Tamami, B.; Lakouraj, M. M. Syn. Commun. 1995, 25, 3089-3096; Huang, Y.; Zhang, Y. ibid. 1996, 26, 2911-2915; Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567-2570; Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. ibid. 1995, 36, 7313-7314; Goulaouic-Dubois, C.; Hesse, M. ibid. 1995, 36, 7427-7430; Salunkhe, A. M.; Brown, H. C. ibid. 1995, 36, 7987-7990; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. ibid. 1996, 37, 4559-4560; Cho, S.-D.; Choi, W.-Y.; Lee, S.-G.; Yoon, Y.-J.; Shin, S. C. ibid. 1996, 37, 7059-7060; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193-1194.
9. 2. For the most recent examples, see: Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254-2256; Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. ibid. 1995, 60, 7682-7683; Tamami, B.; Lakouraj, M. M. Syn. Commun. 1995, 25, 3089-3096; Huang, Y.; Zhang, Y. ibid. 1996, 26, 2911-2915; Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567-2570; Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. ibid. 1995, 36, 7313-7314; Goulaouic-Dubois, C.; Hesse, M. ibid. 1995, 36, 7427-7430; Salunkhe, A. M.; Brown, H. C. ibid. 1995, 36, 7987-7990; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. ibid. 1996, 37, 4559-4560; Cho, S.-D.; Choi, W.-Y.; Lee, S.-G.; Yoon, Y.-J.; Shin, S. C. ibid. 1996, 37, 7059-7060; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193-1194.
10. 2. For the most recent examples, see: Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254-2256; Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. ibid. 1995, 60, 7682-7683; Tamami, B.; Lakouraj, M. M. Syn. Commun. 1995, 25, 3089-3096; Huang, Y.; Zhang, Y. ibid. 1996, 26, 2911-2915; Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567-2570; Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. ibid. 1995, 36, 7313-7314; Goulaouic-Dubois, C.; Hesse, M. ibid. 1995, 36, 7427-7430; Salunkhe, A. M.; Brown, H. C. ibid. 1995, 36, 7987-7990; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. ibid. 1996, 37, 4559-4560; Cho, S.-D.; Choi, W.-Y.; Lee, S.-G.; Yoon, Y.-J.; Shin, S. C. ibid. 1996, 37, 7059-7060; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193-1194.
11. 2. For the most recent examples, see: Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254-2256; Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. ibid. 1995, 60, 7682-7683; Tamami, B.; Lakouraj, M. M. Syn. Commun. 1995, 25, 3089-3096; Huang, Y.; Zhang, Y. ibid. 1996, 26, 2911-2915; Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567-2570; Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. ibid. 1995, 36, 7313-7314; Goulaouic-Dubois, C.; Hesse, M. ibid. 1995, 36, 7427-7430; Salunkhe, A. M.; Brown, H. C. ibid. 1995, 36, 7987-7990; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. ibid. 1996, 37, 4559-4560; Cho, S.-D.; Choi, W.-Y.; Lee, S.-G.; Yoon, Y.-J.; Shin, S. C. ibid. 1996, 37, 7059-7060; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193-1194.
12. 2. For the most recent examples, see: Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254-2256; Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. ibid. 1995, 60, 7682-7683; Tamami, B.; Lakouraj, M. M. Syn. Commun. 1995, 25, 3089-3096; Huang, Y.; Zhang, Y. ibid. 1996, 26, 2911-2915; Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567-2570; Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. ibid. 1995, 36, 7313-7314; Goulaouic-Dubois, C.; Hesse, M. ibid. 1995, 36, 7427-7430; Salunkhe, A. M.; Brown, H. C. ibid. 1995, 36, 7987-7990; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.; Ghosh, A. C. ibid. 1996, 37, 4559-4560; Cho, S.-D.; Choi, W.-Y.; Lee, S.-G.; Yoon, Y.-J.; Shin, S. C. ibid. 1996, 37, 7059-7060; Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193-1194.
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