Cleavage of N-O bonds promoted by samarium diiodide: Reduction of free or N-acylated O-alkylhydroxylamines

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 359-360

  Chiara, José Luis ^a   Destabel, Christine ^a   Gallego, Pilar ^a   Marco Contelles, José ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000237690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951571q     Document Type: Article

References (16)

1. Marco-Contelles, J.; Pozuelo, C.; Jimeno, M. L.; Martínez, L.; Martínez-Grau, A. J. Org. Chem. 1992, 57, 2625.
2. Gilchrist, T. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 8, pp 394-395.
3. Marco-Contelles; Martínez, L.; Martínez-Grau. A. Tetrahedron: Asymmetry 1991, 2, 961 (see also: Ingall, A. H.; Moore, P. R.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1994, 675).
4. Marco-Contelles; Martínez, L.; Martínez-Grau. A. Tetrahedron: Asymmetry 1991, 2, 961 (see also: Ingall, A. H.; Moore, P. R.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1994, 675).
5. Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau. A. Tetrahedron 1993, 49, 6669.
6. For recent reviews on reductions with samarium diiodide, including examples of N-O reductive cleavage, see: (a) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; p 38-39. (b) Molander, G. A. Org. React. 1994, 46, 211.
7. For recent reviews on reductions with samarium diiodide, including examples of N-O reductive cleavage, see: (a) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; p 38-39. (b) Molander, G. A. Org. React. 1994, 46, 211.
8. (a) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
9. (b) Marco-Contelles, J.; Destabel C.; Chiara, J. L ; Bernabé, M. Tetrahedron: Asymmetry 1995, 6, 1547.
10. (a) Keck, G. E.; McHardy, S, F.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289.
11. (b) Keck, G. E.; McHardy, S. F. ; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419.
12. The synthesis of these compounds will be reported elsewhere.
13. 2-promoted reactions in the presence of water, see: Hanessian, S.; Girard, C. Synlett 1994, 861 and references cited therein.
14. 2 in THF and t-BuOH (10 equiv) at room temperature for 16 h produced only 21% of the reduced product (as a mixture with a silyl-migrated analogue, see ref 12), and unreacted 2 was recovered in 57% yield.
15. 3 group.
16. 1H NMR) was obtained in 67% (75% taking into account recovered 2) and 83% yield, respectively, due to partial silyl group migration to nitrogen. Reaction of this mixture with tetra-n-butylammonium fluoride in THF followed by standard acetylation in situ provided the pure compound 7 in ∼90% yield.