Hypervalent iodine oxidation of indolic 2-oxazolines

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 4985-4988

  Braun, Norbert A ^b   Bray, Jonathan D ^a   Ciufolini, Marco A ^a,b  

^a UNIVERSITÉ LYON 1   (France)

^b RICE UNIVERSITY   (United States)

Author keywords

Cyclization; Hypervalent iodine; Indole; Oxazolines; Oxidation

Indexed keywords

INDOLIC 2 OXAZOLINE; IODINE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033516707     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00872-2     Document Type: Article

References (19)

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9. 2) have so far been unsuccessful. This is in accord with observations reported by Kita: Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684-3691. See also reference 3.
10. The balance of the starting material was converted to intractable mixtures of polymeric compounds, thus accounting for the moderate yields of desired products.
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13. (c) Spirocycles related to 12-18 formally derived from indoles: Rodriguez, J. G.; Urrutia, A.; de Diego, J. E.; Martinez-Alcazar, M. P.; Fonseca, I. J. Org. Chem. 1998, 63, 4332-4337.
14. We are grateful to our colleague, Dr. Bernard Fenet, for his assistance with the 2D NOESY measurements.
15. 19F:-74.40,-74.47; [α]=+13.3 (c 0.67).
16. For similar oxidation of phenolic (as opposed to indolic) materials see: (a) Tamura, Y; Yakura, T.; Haruta, J.-I.; Kita, Y. J. Org. Chem. 1987, 52, 3927-3930.
17. (b) Peters, K.; Peters, E.-M.; Braun, N. A.; Ciufolini, M. A. Z. Kristallogr. NCS 1999, 214, 273-274.
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