One-pot selective oxidation/olefination of primary alcohols using TEMPO-BAIB system and stabilized phosphorus ylides

Tetrahedron Letters

Volumn 47, Issue 5, 2006, Pages 715-718

  Vatèle, Jean Michel ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

2,2,6,6 Tetramethyl 1 piperidinyloxy (TEMPO); Bis(acetoxy)iodobenzene (BAIB); Olefination; Oxidation; Unsaturated esters

Indexed keywords

ALCOHOL DERIVATIVE; ESTER DERIVATIVE; PHOSPHORUS DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; OLEFINATION; OXIDATION; STEREOCHEMISTRY; STRUCTURAL HOMOLOGY; SYNTHESIS;

EID: 29544440937     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.100     Document Type: Article

References (19)

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4. 3: C, 68.38; H, 10.59; O, 21.02. Found: C, 68.27; H, 10.71; O, 21.07.
5. In the presence of (carboethoxymethylene)triphenylphosphorane, the ability of the BAIB/TEMPO system to act as an oxidizing agent was inhibited (tested on compounds 1 and 16 ).
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13. 13C NMR.
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15. 3•pyridine (5 equiv) as oxidant, has been very recently published. However, the level of the chemoselectivity is very depending of the structure of the substrates. See: F.R. Pinacho Crisóstomo, R. Carrillo, T. Martin, F. García-Tellado, and V.S. Martin J. Org. Chem. 70 2005 10099 10101
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19. A. Maiti, and J.S. Yadav Synth. Commun. 31 2001 1499 1506 For DMP, see Ref. 8