Direct Conversion of Activated Alcohols to Azides Using Diphenyl Phosphorazidate. A Practical Alternative to Mitsunobu Conditions

Journal of Organic Chemistry

Volumn 58, Issue 22, 1993, Pages 5886-5888

  Thompson, Andrew S ^a   Humphrey, Guy R ^a   DeMarco, Anthony M ^a   Mathre, David J ^a   Grabowski, Edward J J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751385202     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00074a008     Document Type: Article

References (18)

1. Knight, W. B.; Green, B. G.; Chabin, R. M.; Gale, P.; Maycock, A. L.; Weston, H.; Kuo, D. W.; Westler, W. M.; Dorn, C. P.; Finke, P. E.; Hagmann, W. K.; Hale, J. J.; Liesch, J.; MacCoss, M.; Navia, M. A.; Shah, S. K.; Underwood, D.; Doherty, J. B. Biochemistry 1992, 31, 8160.
2. The first example in which an amine equivalent was installed under Mitsunobu conditions used phthalimide as the nucleophile. Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679.
3. The Mitsunobu displacement has been extensively reviewed by Hughes. References to the variation in which a C—N bond is formed can be found in this review; see: Hughes, D. L. Org. React. 1992, 42, 335.
4. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1977, 60, 417.
5. Chen, C.-P.; Prasad, K.; Repic, O. Tetrahedron Lett. 1991, 32, 7175.
6. Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 1977. Using the conditions in which the alcohol and the DEAD/TPP complex are mixed prior to DPPA addition resulted in racemization and olefin formation.
7. Viaud, M. C.; Rollin, P. Synthesis 1990, 130.
8. A similar observation was made in the β-lactam area; see: Gasparski, C. M.; Teng, M.; Miller, M. J. J. Am. Chem. Soc. 1992, 114, 2741.
9. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 2nd ed.; Harper and Row: New York, 1981; p 134.
10. Blacklock, T. J.; Sohar, S.; Butcher, J. W.; Lamanec, T.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 1672.
11. For examples displacing an α-hydroxy ester with an amine equivalent see the following references, (a) Displacement of a tnfluoromethanesulfonate: Effenberger, F.; Burkard, U.; Willfahrt, J. Angew. Chem., Int. Ed. Engl. 1983, 22, 65.
12. 3 see: Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987,190.
13. For an example using a protected hydroxylamine under Mitsunobu conditions see: Kolasa, T.; Miller, M. J. J. Org. Chem. 1987, 52, 4978.
14. Displacement of a p-nitrobenzenesulfonate: Hoffman, R. V.; Kim, H.-O. Tetrahedron 1992, 48, 3007.
15. For the preparation of azido derivatives of amino acids by diazo transfer, see: Zaloom, J.; Roberts, D. C. J. Org. Chem. 1981, 46, 5173.
16. Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880.
17. Yoshioka, M.; Kawakita, T.; Ohno, M. Tetrahedron Lett. 1989, 30, 1657.
18. Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095.