Brønsted acid-promoted olefin aziridination and formal anti-aminohydroxylation

Journal of the American Chemical Society

Volumn 127, Issue 5, 2005, Pages 1354-1355

  Mahoney, Joseph M ^a   Smith, Colin R ^a   Johnston, Jeffrey N ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AZIDE;

ADDITION REACTION; AMINOHYDROXYLATION; ARTICLE; AZIRIDINATION; CATALYSIS; CHEMICAL MODIFICATION; CYCLOADDITION; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY;

EID: 13444302382     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045608c     Document Type: Article

References (29)

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21. For additional examples of triazoline decomposition pathways, see: (a) Wohl, R. A. J. Org. Chem. 1973, 38, 3862 (ring expansions). (b) Goldsmith, D. J.; Soria, J. J. Tetrahedron Lett. 1986, 39, 4701. (c) Hermes, M. E.; Marsh, F. D. J. Org. Chem. 1972, 37, 2969.
22. For additional examples of triazoline decomposition pathways, see: (a) Wohl, R. A. J. Org. Chem. 1973, 38, 3862 (ring expansions). (b) Goldsmith, D. J.; Soria, J. J. Tetrahedron Lett. 1986, 39, 4701. (c) Hermes, M. E.; Marsh, F. D. J. Org. Chem. 1972, 37, 2969.
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28. For the hydrolysis of oxazolidine diones, see: (a) Shapiro, S. L.; Rose, I. M.; Testa, F. C.; Roskin, E.; Freedman, L. J. Am. Chem. Soc. 1959, 81, 6498. (b) Finkbeiner, H. J. Am. Chem. Soc. 1965, 87, 4588.
29. Interestingly, cyclic enones are transformed to their ring-contracted vinylogous amides under similar conditions: Reddy, D. S.; Judd, W. R.; Aubé, J. Org. Lett. 2003, 5, 3899.