Oxidative azidonation of glycals using the reagent combination PhlO/TMSN3: Synthesis of diaminopyrans

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 303-306

  Magnus, Philip ^a   Roe, Michael B ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

FELIS CATUS;

EID: 0030069571     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02158-2     Document Type: Article

References (12)

1. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 767. Magnus, P.; Evans, P. A.; Lacour, J. Tetrahedron Lett 1992, 33 , 2933.
2. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 767. Magnus, P.; Evans, P. A.; Lacour, J. Tetrahedron Lett 1992, 33 , 2933.
3. Magnus, P.; Roe, M. B.; Hulme, C. J. C. S. Chem. Comm., 1995, 263. Magnus, P.; Barth, L. Tetrahedron Lett 1992, 33, 2777.
4. Magnus, P.; Roe, M. B.; Hulme, C. J. C. S. Chem. Comm., 1995, 263. Magnus, P.; Barth, L. Tetrahedron Lett 1992, 33, 2777.
5. Kirschning, A.; Domann, S.; Dräger, G.; Rose, L. Synlett 1995, 767. Kirschning, A. J. Org. Chem. 1995, 60, 1228.
6. Kirschning, A.; Domann, S.; Dräger, G.; Rose, L. Synlett 1995, 767. Kirschning, A. J. Org. Chem. 1995, 60, 1228.
7. The α-azidonation reaction in the presence of TEMPO produces by-product(s) that result from the anomeric radical combining with TEMPO to give a covalent adduct. In the example of 6 we have isolated 6a in 7% yield, which corresponds to 70% based on the amount of TEMPO present. (equation presented)
8. Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809. Czernecki, S.; Randriamandimby, D. Tetrahedron Lett 1993, 34, 7915. Santoyo-González, F.; Calvo-Flores, F. G.; García-Mendoza, P.; Herńndez-Mateo, F.; Isac-García, J.; Robles-Díaz, R. J. Org. Chem. 1993, 59, 6122.
9. Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809. Czernecki, S.; Randriamandimby, D. Tetrahedron Lett 1993, 34, 7915. Santoyo-González, F.; Calvo-Flores, F. G.; García-Mendoza, P.; Herńndez-Mateo, F.; Isac-García, J.; Robles-Díaz, R. J. Org. Chem. 1993, 59, 6122.
10. Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809. Czernecki, S.; Randriamandimby, D. Tetrahedron Lett 1993, 34, 7915. Santoyo-González, F.; Calvo-Flores, F. G.; García-Mendoza, P.; Herńndez-Mateo, F.; Isac-García, J.; Robles-Díaz, R. J. Org. Chem. 1993, 59, 6122.
11. We have detected small amounts of allylic azide isomers (anomeric azide) corresponding to 31 in the reactions to give 5, 19 and 21, and we have not observed subsequent allylic rearrangement of these azides.
12. We have frequently observed that the β-azido group can be ionized in the presence of a Lewis acid, Jérôme Lacour, Ph. D thesis, The University of Texas at Austin, 1993.